Methylamine → methyl 3-(N-methylsulfamoyl)thiophene-2-carboxylate

HRID 59734

Reaction equation

HRID 59734 reaction equation
Cl[S:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].C1COCC1.[CH3:19][NH2:20]>C(Cl)Cl>[CH3:19][NH:20][S:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Product 1

HCID 12906749methyl 3-(N-methylsulfamoyl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(chlorosulfonyl)thiophene-2-carboxylate (500 mg, 2.077 mmol) in DCM (20 ml), methanamine 2N solution in THF (4.155 ml, 8.31 mmol) was added and the reaction was stirred for 1 hour at RT. The mixture was partitioned between 2N HCl and DCM and the aqueous phase was extracted with DCM. The combined organic layers were dried over sodium sulfate and the solvent was removed affording methyl 3-(N-methylsulfamoyl)thiophene-2-carboxylate (Int. 32) (430 mg, 1.828 mmol, MS/ESI+235.8 [MH]+).

Workup

  1. customThe mixture was partitioned between 2N HCl and DCM
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-9b66d920a79c456da03aea4e17f10758
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Linked notes

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