Chlorosulfonic acid → 4-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride

HRID 1746669

反応式

HRID 1746669 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[O:9])[CH:3]=1.[Cl:18][S:19](O)(=[O:21])=[O:20]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:19]([Cl:18])(=[O:21])=[O:20])=[CH:13][C:12]=2[CH3:17])=[O:9])[CH:3]=1

参加物

4

反応物 2

HCID 24638Chlorosulfonic acidHCID 594470936-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide2 回

生成物 1

HCID 594468454-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A cooled (0° C.) solution of 6-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 18; 14.00 g; 56.52 mmol) in DCM (280 ml) was treated dropwise with a solution of chlorosulfonic acid (37.8 ml; 565 mmol) in DCM (100 mL). The reaction mixture was allowed to warm from 0° C. to room temperature, then it was stirred at room temperature overnight. The mixture was cooled to 15° C., a mixture ice/water was added and it was stirred for a few minutes. Phases were separated and the organic layer was washed with cold water, brine, dried over MgSO4, filtered and concentrated under vacuum to afford the title compound as a beige solid.

後処理

  1. temperatureto warm from 0° C. to room temperature
  2. temperatureThe mixture was cooled to 15° C.
  3. stirringit was stirred for a few minutes
  4. customPhases were separated
  5. washthe organic layer was washed with cold water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-33861456a9e24069b46105b31d7aed97
出典データセット
uspto-grants-2015_10
特許番号
US09150519B2

関連ノート

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