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

HRID 28005

Reaction equation

HRID 28005 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](Cl)(=[O:12])=[O:11])=[O:4].C(Cl)(Cl)Cl.[CH3:18][NH2:19]>O>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:12])(=[O:11])[NH:19][CH3:18])=[O:4]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6329MethylamineHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

43.5 G. (0.18 mol) of the obtained 3-chlorosulfonylthiophene-2-carboxylic acid methyl ester are dissolved in 450 ml. of absolute chloroform and dry methylamine is led through the solution at 10° C. until a moistened pH paper shows an alkaline reaction with the solution. The mixture is then allowed to react at room temperature for a further 2 hours, the solution always remaining alkaline. The solution is then shaken out with 500 ml. of water and 500 ml. of a 5% sodium bicarbonate solution [the aqueous phases are back-extracted in each case once with chloroform]. The combined organic phases are dried over sodium sulfate and then evaporated. The crystalline residue is digested with ether for purification. There is obtained 3-methylsulfamoylthiophene-2-carboxylic acid methyl ester of melting point 115°-122° C.

Workup

  1. customis led through the solution at 10° C. until a moistened pH paper
  2. customan alkaline reaction with the solution
  3. customto react at room temperature for a further 2 hours
  4. extractionof a 5% sodium bicarbonate solution [the aqueous phases are back-extracted in each case once with chloroform]
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated
  7. customThe crystalline residue is digested with ether for purification

Sources & evidence

ORD record
ord-cfd42209e65a4dbbbd28443a132897ca
Source dataset
uspto-grants-1980_09
Patent number
US04224445

Linked notes

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