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

HRID 59731

반응식

HRID 59731 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매2회HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-54ef70fbb3f7410181abd27a6f8a2096
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

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