Methyl 3-amino-2-thiophenecarboxylate → Methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylate

HRID 59761

Reaction equation

HRID 59761 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:11][N:12]([CH3:25])[C:13]([C:15]1[CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1)=[O:14]>Cl>[CH3:11][N:12]([CH3:25])[C:13]([C:15]1[CH:16]=[C:17]([S:21]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1)=[O:14]

Participants

4

Reactant 2

HCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 180721433-(Dimethylcarbamoyl)benzene-1-sulfonyl chloride

Product 1

HCID 86703867Methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 3-aminothiophene-2-carboxylate (93 mg, 0.592 mmol) was dissolved in Py (1.5 ml). 3-(dimethylcarbamoyl)benzene-1-sulfonyl chloride (220 mg, 0.887 mmol) was added, and the reaction was stirred at RT for 3 hrs to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with AcOEt. The organic phase was washed with HCl 1N and brine, dried over Na2SO4 and concentrated under vacuum to give methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylate (Int. 79, 200 mg, 0.543 mmol).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic phase was washed with HCl 1N and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4b9a69ee2c1049b9bd58d7c8d5660f84
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Linked notes

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