Water → 5-Chloro-1,3-dihydro-1-(3,4-dimethoxybenzenesulfonyl)-3-phenyl-2H-benzimidazol-2-one

HRID 1081492ノート

反応式

HRID 1081492 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30](Cl)(=[O:32])=[O:31])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].O>CN(C=O)C>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[N:8]([S:30]([C:24]3[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=3)(=[O:32])=[O:31])[C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1086532H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-phenyl-HCID 27341833,4-Dimethoxybenzenesulfonyl chloride

生成物 1

HCID 152315405-Chloro-1,3-dihydro-1-(3,4-dimethoxybenzenesulfonyl)-3-phenyl-2H-benzimidazol-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

66 mg of sodium hydride as an 80% dispersion in oil were added in portions to a solution of 490 mg of 5-chloro-1,3-dihydro-3-phenyl-2H-benzimidazol-2-one in 5 ml of DMF and the reaction medium was stirred for 30 minutes. 520 mg of 3,4-dimethoxybenzenesulfonyl chloride were then introduced and the reaction medium was stirred overnight at room temperature. The solvent was then evaporated off under vacuum and the residue obtained was taken up with water. It was then extracted with DCM, washed with water and then dried over sodium sulfate and the solvent was evaporated off to dryness. The residue obtained was chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product in the form of a white solid, which crystallized from absolute EtOH. m=0.71 g. M.p.=154° C.

後処理

  1. stirringthe reaction medium was stirred overnight at room temperature
  2. customThe solvent was then evaporated off under vacuum
  3. customthe residue obtained
  4. extractionIt was then extracted with DCM
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated off to dryness
  8. customThe residue obtained
  9. customwas chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent

出典と根拠

ORDレコード
ord-705fa175bcf64a5bb64f2447194325ca
出典データセット
uspto-grants-1996_12
特許番号
US05585394

反応ノート

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