Triethylamine → HCID 54431177, compound

HRID 1834732Notes

Reaction equation

HRID 1834732 reaction equation
[C:1]1([NH:7][S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:20][CH:21]([Cl:29])[C:22]([Cl:28])([S:24](Cl)(=O)=O)[CH3:23]>C(Cl)(Cl)Cl>[Cl:20][CH:21]([Cl:29])[C:22]([Cl:28])([S:24][N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 767447N-phenylethanesulfonamideHCID 20324730HCID 20324730, compound

Product 1

HCID 54431177HCID 54431177, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred, cooled solution of 18.5 g. of N-phenyl ethane sulfonamide in 10.1 g. of triethylamine and 200 ml. of chloroform was added at a temperature below 10° C. a solution of 1,1,2-trichloropropane-2-sulfonyl chloride (21.4 g.) in 50 ml. of chloroform. During the addition, an exothermic reaction took place. When the addition was complete, the mixture was allowed to cool to room temperature. The product was washed twice with water, dried over sodium sulfate and filtered and stripped. A viscous red oil was formed which on evaporation with benzene yielded a solid product of 29.6 g. (92% of theory), m.p. 85°-86° C.

Workup

  1. temperatureTo a stirred, cooled solution of 18.5 g
  2. additionDuring the addition
  3. customan exothermic reaction
  4. additionWhen the addition
  5. washThe product was washed twice with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customA viscous red oil was formed which
  9. customon evaporation with benzene
  10. customyielded a solid product of 29.6 g

Sources & evidence

ORD record
ord-b128be77c4b749b8a8cb161d3fa50358
Source dataset
uspto-grants-1978_01
Patent number
US04071352

Reaction notes

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