Methanesulfonyl chloride → Ethyl 4-(methylsulfonamido)thiophene-2-carboxylate

HRID 59740Notes

Reaction equation

HRID 59740 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:5][CH:6]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[CH3:12][S:13]([NH:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:5][CH:6]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22418292Ethyl 4-aminothiophene-2-carboxylate

Product 1

HCID 86703842Ethyl 4-(methylsulfonamido)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 4-aminothiophene-2-carboxylate (Int. 41) (theoretical 1.785 mmol) in pyridine (20 ml), methanesulfonyl chloride (0.239 ml, 3.07 mmol) was added and the mixture was stirred overnight at RT. The solvent was evaporated and the residue was partitioned between 1N HCl and EtOAc; the aqueous phase was extracted with EtOAc and the combined organic layers were dried over sodium sulfate and evaporated to afford ethyl 4-(methylsulfonamido)thiophene-2-carboxylate (Int. 42) which was used without any additional purification (370 mg, 1.484 mmol, MS/ESI+249.8 [MH]+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between 1N HCl and EtOAc
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-17b71bdba61442fb8c25b3ca0c7c4eaa
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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