Thionyl Chloride → 4-(3-Chloro-4-methoxybenzylamino)-5-chloroformyl-6-chloro-2-methylthiopyrimidine

HRID 917647Notes

Reaction equation

HRID 917647 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:5][NH:6][C:7]1[C:12]([C:13](O)=[O:14])=[C:11]([Cl:16])[N:10]=[C:9]([S:17][CH3:18])[N:8]=1.S(Cl)([Cl:26])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:5][NH:6][C:7]1[C:12]([C:13]([Cl:26])=[O:14])=[C:11]([Cl:16])[N:10]=[C:9]([S:17][CH3:18])[N:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 178482684-(3-Chloro-4-methoxybenzylamino)-5-carboxy-6-chloro-2-methylthiopyrimidine

Product 1

HCID 178482834-(3-Chloro-4-methoxybenzylamino)-5-chloroformyl-6-chloro-2-methylthiopyrimidine

Conditions

Temperature
75 °C

Procedure

A mixture of 4-(3-chloro-4-methoxybenzylamino)-5-carboxy-6-chloro-2-methylthiopyrimidine 10.50 g and thionyl chloride 25 ml is stirred for 20 minutes at 75° C. After reaction thionyl chloride is distilled off and the solvent is removed by azeotrope with methylene chloride to give 4-(3-chloro-4-methoxybenzylamino)-5-chloroformyl-6-chloro-2-methylthiopyrimidine.

Workup

  1. distillationis distilled off
  2. customthe solvent is removed by azeotrope with methylene chloride

Sources & evidence

ORD record
ord-2ab45cefda854a9090333697c9badf06
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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