Peracetic acid; Peroxyacetic acid -Drug Synthesis Database

【结构式】

【分子编号】54916

【品名】Peracetic acid; Peroxyacetic acid

【CA登记号】79-21-0

【分子式】C₂H₄O₃

【分子量】76.05196

【元素组成】C 31.59% H 5.3% O 63.11%

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：(VIII)

The acetylation of 2,3,5-trimethyl-4-nitropyridine N-oxide (I) with acetic anhydride in hot acetic acid gives the 2-(acetoxymethyl)-3,5-dimethyl-4-nitropyridine (II), which, without isolation, is treated with NaOH in hot dichloromethane/water, yielding the corresponding 2-(hydroxymethyl) derivative (III). This compound, also without isolation, is treated with SOCl2 to afford 2-(chloromethyl)-3,5-dimethyl-4-nitropyridine (IV), which is condensed with 6-methoxy-1H-benzimidazole-2-thiol (V) by means of tetrabutylammonium bromide and NaOH in dichloromethane/water, providing the corresponding thioether (VI). The reaction of (VI) with sodium methoxide and K2CO3 in refluxing methanol yields 5-methoxy-2-(4-methoxy-3,5-dimethylpyridin-2-ylmethylsulfanyl)-1H-benzimidazole (VII), which is finally oxidized to the target sulfoxide with peracetic acid (VIII) in ethyl acetate.

参考文献中间体

合成目标

【1】 Hamied, Y.K.; Kankan, R.N.; Rao, D.R. (Cipla Ltd.); Omeprazole synthesis. EP 1085019 .

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)	54909	2,3,5-trimethyl-4-nitro-1-pyridiniumolate		C₈H₁₀N₂O₃	详情	详情
(II)	54910	(3,5-dimethyl-4-nitro-2-pyridinyl)methyl acetate		C₁₀H₁₂N₂O₄	详情	详情
(III)	54911	3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine		C₈H₁₀N₂O₃	详情	详情
(IV)	54912	2-(chloromethyl)-3,5-dimethyl-4-nitropyridine		C₈H₉ClN₂O₂	详情	详情
(V)	54913	6-methoxy-1H-benzimidazol-2-ylhydrosulfide; 6-methoxy-1H-benzimidazole-2-thiol		C₈H₈N₂OS	详情	详情
(VI)	54914	2-{[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfanyl}-1H-benzimidazol-6-yl methyl ether; 2-{[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfanyl}-6-methoxy-1H-benzimidazole		C₁₆H₁₆N₄O₃S	详情	详情
(VII)	54915	2-{[(6-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl}-3,5-dimethyl-4-pyridinyl methyl ether; 6-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfanyl}-1H-benzimidazole		C₁₇H₁₉N₃O₂S	详情	详情
(VIII)	54916	Peracetic acid; Peroxyacetic acid	79-21-0	C₂H₄O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The oxidation of p-chloroiodobenzene (I) with peracetic acid (II) in acetic acid affords 4-chloroiodosobenzene diacetate (III), which is then condensed with thiophene (IV) by means of acetic anhydride and trifluoroacetic acid yielding (p-chlorophenyl)-2-thienyliodonium trifluoroacetate (V). Finally this salt is treated with HCl in aqueous formic acid. (1-4)

参考文献中间体

合成目标

【1】 Moyle, C.L. (Dow Chem. Co.); US 3885036 .
【2】 Castaner, J.; Blancafort, P.; Tiodonium chloride. Drugs Fut 1977, 7, 6, 407.
【3】 Moyle, C.L. (Dow Chem. Co.); DE 2145733; GB 1351531 .
【4】 Moyle, C.L. (Dow Chem. Co.); US 3763187 .
【5】 Moyle, C.L. (Dow Chem. Co.); FR 2153532 .

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)	19395	1-chloro-4-iodobenzene	637-87-6	C₆H₄ClI	详情	详情
(II)	54916	Peracetic acid; Peroxyacetic acid	79-21-0	C₂H₄O₃	详情	详情
(III)	60922	bis(acetyloxy)(4-chlorophenyl)-lambda~3~-iodane		C₁₀H₁₀ClIO₄	详情	详情
(IV)	13297	Thiophene	110-02-1	C₄H₄S	详情	详情
(V)	60923	(4-chlorophenyl)(2-thienyl)iodonium		C₁₂H₇ClF₃IO₂S	详情	详情

Extended Information