Sodium Hydroxide → methyl 1-(3-(dimethylcarbamoyl)-4-methoxyphenylsulfonyl)-1H-pyrrole-2-carboxylate

HRID 59731

反応式

HRID 59731 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[OH-].[Na+].[CH3:12][N:13]([CH3:28])[C:14]([C:16]1[CH:17]=[C:18]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])=[O:15]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[CH3:28][N:13]([CH3:12])[C:14]([C:16]1[CH:17]=[C:18]([S:24]([N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][CH3:9])=[O:7])(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])=[O:15]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 136930Methyl pyrrole-2-carboxylateHCID 457912293-(Dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride

生成物 1

HCID 86703837methyl 1-(3-(dimethylcarbamoyl)-4-methoxyphenylsulfonyl)-1H-pyrrole-2-carboxylate収率 65.7%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒3 回

実験手順

To a mixture of methyl 1H-pyrrole-2-carboxylate (135 mg, 1.080 mmol), tetrabutylammonium hydrogensulfate (36.7 mg, 0.108 mmol) and sodium hydroxide (389 mg, 9.72 mmol) in water (2 ml) and DCM (4 ml) under vigorous stirring, a solution of 3-(dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride (Int. 9) (300 mg, 1.080 mmol) in DCM (5 ml) was added drop-wise at RT over 10 minutes, and the reaction was stirred at the same temperature for 24 hours. The mixture was diluted with water and DCM, the organic phase was separated, washed with brine and dried over sodium sulfate. The solvent was evaporated under vacuum yielding methyl 1-(3-(dimethylcarbamoyl)-4-methoxyphenylsulfonyl)-1H-pyrrole-2-carboxylate (Int. 10) (260 mg, 0.710 mmol, MS/ESI+367.0 [MH]+) which was used as such in the next step.

後処理

  1. customthe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-54ef70fbb3f7410181abd27a6f8a2096
出典データセット
uspto-grants-2016_09
特許番号
US09440954B2

関連ノート

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