methyl cyanocarbamate -Drug Synthesis Database

【结构式】

【分子编号】33600

【品名】methyl cyanocarbamate

【CA登记号】

【分子式】C₃H₄N₂O₂

【分子量】100.07704

【元素组成】C 36.01% H 4.03% N 27.99% O 31.97%

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：(B)

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：(VI)

Alkylation of 4-hydroxyacetanilide (I) with n-propyl bromide provided 4-propoxyacetanilide (II). Aromatic nitration of (II) with fuming nitric acid in the presence of acetic anhydride afforded the nitro acetanilide (III), which was further hydrolyzed to the nitro aniline (IV) under basic conditions. Subsequent catalytic hydrogenation of the nitro group of (IV) furnished the phenylenediamine (V). Cyanocarbamate (VI), generated from cyanamide and methyl chloroformate, was then condensed with 4-propoxy-1,2-phenylenediamine (V) in hot pyridine to provide the title benzimidazolyl carbamate.

参考文献中间体

合成目标

【1】 Castaner, J.; Bogan, J.A.; Oxibendazole. Drugs Fut 1976, 1, 5, 255.
【2】 Actor, P.P.; Pagano, J.F. (GlaxoSmithKline Inc.); Anthelmintic compsns. and methods employing esters of benzimidazolyl carbamic acids and their thio analogs. BE 0666795; BE 0691611; CH 479590; DE 1620439; DE 1795799; FR 1510235; GB 1096190; GB 1114069; GB 1123317; US 3574845 .

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)	21611	4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide	103-90-2	C₈H₉NO₂	详情	详情
(II)	59302	N-(4-propoxyphenyl)acetamide		C₁₁H₁₅NO₂	详情	详情
(III)	59303	N-(2-nitro-4-propoxyphenyl)acetamide		C₁₁H₁₄N₂O₄	详情	详情
(IV)	59304	2-nitro-4-propoxyaniline; 2-nitro-4-propoxyphenylamine		C₉H₁₂N₂O₃	详情	详情
(V)	59305	2-amino-4-propoxyphenylamine; 4-propoxy-1,2-benzenediamine		C₉H₁₄N₂O	详情	详情
(VI)	33600	methyl cyanocarbamate		C₃H₄N₂O₂	详情	详情

Extended Information