2-Thiophenesulfonyl chloride → Methyl 5-methyl-4-[(2-thienylsulfonyl)amino]thiophene-2-carboxylate

HRID 453570Notes

Reaction equation

HRID 453570 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[S:5][C:6]=1[CH3:7].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:7][C:6]1[S:5][C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:3][C:2]=1[NH:1][S:17]([C:13]1[S:12][CH:16]=[CH:15][CH:14]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 59640747Methyl 4-amino-5-methylthiophene-2-carboxylate

Product 1

HCID 59411395Methyl 5-methyl-4-[(2-thienylsulfonyl)amino]thiophene-2-carboxylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of methyl 4-amino-5-methylthiophene-2-carboxylate (20 g) and pyridine (100 mL) was added 2-thiophen-sulfonyl chloride (23.5 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give methyl 5-methyl-4-[(2-thienylsulfonyl)amino]thiophene-2-carboxylate (35.7 g, yield 96%) as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f98ef8475d544d2f9dc0ff43e6baba46
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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