propylhydrosulfide; 1-propanethiol -Drug Synthesis Database

【结构式】

【分子编号】23703

【品名】propylhydrosulfide; 1-propanethiol

【CA登记号】107-03-9

【分子式】C₃H₈S

【分子量】76.16252

【元素组成】C 47.31% H 10.59% S 42.1%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(A)

The condensation of 3-chloro-6-nitroacetanilide (I) with propylmercaptane (A) by means of aqueous refluxing NaOH gives 2-nitro-5-propylthioaniline (II), which was reduced with H2 over Pd/C in ethanol HCl to yield 4-propylthio-o-phenylenediamine (III). The cyclization of (III) with cyanogen bromide affords 2-amino-5-propylthiobenzimidazole (IV), which is finally condensed with methyl chloroformate. It can be condensed directly with a mixture of cyanamide and methyl chloroformate or with carbomethoxycyanamide (B). All these condensations are performed in basic medium.

参考文献中间体

合成目标

【1】 Gyurik, R.J.; Theodorides, V.J.; Methyl 5-propylthio-2-benzimidazolecarbamate. DE 2527065; FR 2275203; GB 1464326; JP 51012936; US 3915986 .
【2】 Bogan, J.; Castaner, J.; Albendazole. Drugs Fut 1977, 2, 2, 81.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	23703	propylhydrosulfide; 1-propanethiol	107-03-9	C₃H₈S	详情	详情
(B)	33600	methyl cyanocarbamate		C₃H₄N₂O₂	详情	详情
(I)	25241	N-(5-chloro-2-nitrophenyl)acetamide	39163-92-3	C₈H₇ClN₂O₃	详情	详情
(II)	33597	2-nitro-5-(propylsulfanyl)phenylamine; 2-nitro-5-(propylsulfanyl)aniline		C₉H₁₂N₂O₂S	详情	详情
(III)	33598	4-(propylsulfanyl)-1,2-benzenediamine; 2-amino-4-(propylsulfanyl)phenylamine; 2-Amino-5-propylthioaniline	66608-52-4	C₉H₁₄N₂S	详情	详情
(IV)	33599	5-(propylsulfanyl)-1H-benzimidazol-2-ylamine; 5-(propylsulfanyl)-1H-benzimidazol-2-amine		C₁₀H₁₃N₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Acylation of Meldrum's acid (I) with propionyl chloride (II) in the presence of pyridine gave propionyl derivative (III). Subsequent ring opening of (III) with propanethiol (IV), followed by decarboxylation provided S-propyl 3-oxothiovalerate (V). Propyl 3-amino-3-(m-chlorophenyl)-2-propenoate (VII) was prepared by reaction of (3-chlorobenzoyl)acetate (VI) with ammonium acetate in refluxing ethanol. Then, Hantzsch condensation of ketothioester (V), beta-enaminoester (VII), and propionaldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX). Finally, oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.

参考文献中间体

合成目标

【1】 Li, A.-H.; Moro, S.; Melman, N.; Ji, X.D.; Jacobson, K.A.; Structure-activity relationships and molecular mod. J Med Chem 1998, 41, 17, 3186.

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)	14738	Meldrum's acid; 2,2-dimethyl-1,3-dioxane-4,6-dione；Malonic acid cyclic isopropylidene ester	2033-24-1	C₆H₈O₄	详情	详情
(II)	15967	propanoyl chloride; propionyl chloride	79-03-8	C₃H₅ClO	详情	详情
(III)	23689	2,2-dimethyl-5-propionyl-1,3-dioxane-4,6-dione		C₉H₁₂O₅	详情	详情
(IV)	23703	propylhydrosulfide; 1-propanethiol	107-03-9	C₃H₈S	详情	详情
(V)	23704	S-propyl 3-oxopentanethioate		C₈H₁₄O₂S	详情	详情
(VI)	23705	propyl 3-(3-chlorophenyl)-3-oxopropanoate		C₁₂H₁₃ClO₃	详情	详情
(VII)	23706	propyl (E)-3-amino-3-(3-chlorophenyl)-2-propenoate		C₁₂H₁₄ClNO₂	详情	详情
(VIII)	15966	propionaldehyde	123-38-6	C₃H₆O	详情	详情
(IX)	23708	propyl 2-(3-chlorophenyl)-4,6-diethyl-5-[(propylsulfanyl)carbonyl]-1,4-dihydro-3-pyridinecarboxylate		C₂₃H₃₀ClNO₃S	详情	详情
(X)	21891	2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil	118-75-2	C₆Cl₄O₂	详情	详情

Extended Information