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

HRID 59731

Reaction equation

HRID 59731 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-54ef70fbb3f7410181abd27a6f8a2096
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Linked notes

Loading…