4-Methoxyphenyl isothiocyanate → 1-(2,2-Dimethoxyethyl)-3-(4-methoxyphenyl)thiourea

HRID 981565ノート

反応式

HRID 981565 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[S:11])=[CH:5][CH:4]=1.[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH2:16]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([NH:16][CH2:15][CH:14]([O:17][CH3:18])[O:13][CH3:12])=[S:11])=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 752934-Methoxyphenyl isothiocyanateHCID 89728Aminoacetaldehyde dimethyl acetal

生成物 1

HCID 8820791-(2,2-Dimethoxyethyl)-3-(4-methoxyphenyl)thiourea

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 10 g (.06 mole) of p-methoxyphenyl isothiocyanate in 100 ml of CHCl3 was treated with 6.3 g (.06 mole) of aminoacetaldehyde dimethyl acetal. The solvent was evaporated and the residue was recrystallized from ethanol to yield N-(p-methoxyphenyl)-N'-(β,β-dimethoxyethyl)thiourea, 9.2 g (57%). A suspension of this thiourea in a solution of 5 ml of concentrated H2SO4 and 20 ml of H2O was refluxed for 3 hours. The mixture was cooled and a solid was filtered, washed with H2O and dried. Recrystallization from ethanol gave 1-(4-methoxyphenyl)-2-mercaptomidazole, 4.9 g (70%), mp 215-7° . The compound can be deprotected, for example, as illustrated in Example 5 and 6, below, to prepare the phenol, Y is --OH.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-1fd650ff0d164c38b99308cdb89af77e
出典データセット
uspto-grants-1991_02
特許番号
US04992459

反応ノート

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