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【结 构 式】

【分子编号】19538

【品名】5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole

【CA登记号】7305-71-7

【 分 子 式 】C4H6N2S

【 分 子 量 】114.17112

【元素组成】C 42.08% H 5.3% N 24.54% S 28.09%

与该中间体有关的原料药合成路线共 7 条

合成路线1

该中间体在本合成路线中的序号:(III)

The synthesis of meloxicam is performed as follows: The reaction of benzisothiazolo-3(2H)-one-1,1-dioxide (I) with methyl chloroacetate gives the methyl 2(3H)-acetate derivative, which is isomerized with sodium methoxide in toluene/tert-butanol yielding methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide. The subsequent methylation with methyl iodide in methanol yields 2-methyl compound (II). Finally, this compound is treated with 2-amino-5-methylthiazole in xylene.

1 Trummlitz, G.; Engelhardt, G.; Busch, U.; MELOXICAM < Rec INN >. Drugs Fut 1989, 14, 11, 1047.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11298 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin 81-07-2 C7H5NO3S 详情 详情
(II) 19537 methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C11H11NO5S 详情 详情
(III) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

 

1 Zia-ur-Rehman M, Choudary JA, Ahmad S 2005. Applied chemistry research center, lahore, pak. An efficient synthysis of 2-alkyl-4-hydroxy2H-l, 2-benzothiazine-3-carboxamide-l, l-dioxides. Bull Korean Chem Soc, 26: 1771~1775
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 40062 methyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate 6639-62-9 C10H9NO5S 详情 详情
(II) 66516 methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide 35511-14-9 C10H9NO5S 详情 详情
(III) 19537 methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C11H11NO5S 详情 详情
(IV) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情

合成路线3

该中间体在本合成路线中的序号:(V)

 

1 Wu,Fan-hong Wang,Bao-dan. Xi,Guan-gen.2002.Synthesis of meloxicam and piroxicam.华东理工大学学报,28: 282~284
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11298 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin 81-07-2 C7H5NO3S 详情 详情
(II) 66518 isopropyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetate   C12H13NO5S 详情 详情
(III) 66519 isopropyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide 76508-35-5 C12H13NO5S 详情 详情
(IV) 66519 isopropyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide 76508-35-5 C12H13NO5S 详情 详情
(V) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情

合成路线4

该中间体在本合成路线中的序号:(IV)

 

1 Wang YC, Shi DQ, Zhao H et aL.2001. Synthesis of meloxicam. 中国医药工业杂志.32: 244~245
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 29338 1-propanol 71-23-8 C3H8O 详情 详情
(II) 15966 propionaldehyde 123-38-6 C3H6O 详情 详情
(III) 66520 3,3-dibromopropanal   C3H4Br2O 详情 详情
(IV) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情
(V) 19537 methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C11H11NO5S 详情 详情

合成路线5

该中间体在本合成路线中的序号:(V)

 

1 Zhang L. Xie LH,Hua ZM et aL 2000.Synthesis of meloxicanm. 中国医药工业杂志,31: 481~483
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 66519 isopropyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide 76508-35-5 C12H13NO5S 详情 详情
(I) 11298 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin 81-07-2 C7H5NO3S 详情 详情
(II) 40062 methyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate 6639-62-9 C10H9NO5S 详情 详情
(III) 66516 methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide 35511-14-9 C10H9NO5S 详情 详情
(V) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情

合成路线6

该中间体在本合成路线中的序号:(II)

 

1 Trummlitz G, Engel W, Seeger E et aL 1980. 4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide-l,l-dioxides and salts thereof. US 4233299
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 19537 methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C11H11NO5S 详情 详情
(II) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情

合成路线7

该中间体在本合成路线中的序号:(VI)

 

1 Hill JH M. 1965. Mechanism of the gabriel-colman rearrangement. J Org Chem, 30: 620~622
2 Wen YZ, Wei WL, Gao ZW. 2005. Synthesis of meloxicam.中国医药工业杂志.36 (6): 321~322
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 66516 methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide 35511-14-9 C10H9NO5S 详情 详情
(I) 66521     C7H4KN2O3 详情 详情
(II) 10257 methyl 2-chloroacetate; methyl chloroacetate 96-34-4 C3H5ClO2 详情 详情
(III) 66522     C10H9N2O5 详情 详情
(V) 19537 methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C11H11NO5S 详情 详情
(VI) 19538 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 7305-71-7 C4H6N2S 详情 详情
Extended Information