Methylamine → 2,5-Dichloro-N-methyl-3-thiophenesulfonamide

HRID 1448584Notes

Reaction equation

HRID 1448584 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[CH:5][C:6]=1[S:7](Cl)(=[O:9])=[O:8].[CH3:12][NH2:13]>C(Cl)(Cl)Cl>[CH3:12][NH:13][S:7]([C:6]1[CH:5]=[C:4]([Cl:11])[S:3][C:2]=1[Cl:1])(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27360942,5-Dichlorothiophene-3-sulfonyl chloride

Product 1

HCID 105623432,5-Dichloro-N-methyl-3-thiophenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3500 ml. of absolute chloroform are placed in a 4 liter volume flask and 533 g. of 2,5-dichlorothiophene-3-sulfonic acid chloride are dissolved therein. Dry methylamine is passed in at 20° with stirring until the solution gives a basic reaction with moistened indicator paper. The solution is stirred for an additional 11/2 hours at room temperature, then extracted several times with 0.5 N HCl in a separating funnel, dried with anhydrous sodium sulfate, and finally concentrated by evaporation in vacuo. The oil thus obtained is placed in a low temperature container, where it crystallizes. The product thus obtained is purified by recrystallization from 1500 ml. of carbon tetrachloride, is dried in a vacuum drying cabinet at 40° and 2,5-dichlorothiophene-3-sulfonic acid methylamide having a melting point of 59°-61° is obtained.

Workup

  1. customis passed in at 20°
  2. customgives
  3. customa basic reaction with moistened indicator paper
  4. stirringThe solution is stirred for an additional 11/2 hours at room temperature
  5. extractionextracted several times with 0.5 N HCl in a separating funnel
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationfinally concentrated by evaporation in vacuo
  8. customThe oil thus obtained
  9. customcrystallizes
  10. customThe product thus obtained
  11. customis purified by recrystallization from 1500 ml
  12. dry with materialof carbon tetrachloride, is dried in a vacuum
  13. customdrying cabinet at 40°

Sources & evidence

ORD record
ord-5f29b6e7309a47a9886e6d12a3a4bf4e
Source dataset
uspto-grants-1979_12
Patent number
US04180662

Reaction notes

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