Dimethylamine → HCID 20215695, compound

HRID 236513Notes

Reaction equation

HRID 236513 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH3:12][NH:13][CH3:14]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:13]([CH3:14])[CH3:12])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 761872-Chlorobenzenesulfonyl chloride

Product 1

HCID 20215695HCID 20215695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 63.3 g of 2-chlorobenzensulfonyl chloride in 500 mL of tetrahydrofuran was cooled to 0°-5° C. and treated with 46 mL of dimethylamine, added dropwise at a rate that maintained the temperature below 10° C. The resulting mixture was allowed to warm gradually to room temperature. The precipitate was removed by filtration, and was washed well with tetrahydrofuran. The combined filtrates were evaporated in vacuo and the resulting oil was dissolved in 400 mL of methylene chloride, washed with two 200-mL portions of water, and dried over MgSO4. Evaporation of the solvent in vacuo afforded an oil, which solidified upon standing. Trituration with hexanes afforded 58.6 g of 2-chloro-N,N-dimethylbenzenesulfonamide as a white solid, m.p. 49°-51° C.; NMR (CDCl3): δ2.9 (s, 6H), 7.3-7.7 and 7.9-8.2 (m, 4H); IR(KBr): 1340 and 1170 cm-1.

Workup

  1. additionadded dropwise at a rate that
  2. temperaturemaintained the temperature below 10° C
  3. customThe precipitate was removed by filtration
  4. washwas washed well with tetrahydrofuran
  5. customThe combined filtrates were evaporated in vacuo
  6. dissolutionthe resulting oil was dissolved in 400 mL of methylene chloride
  7. washwashed with two 200-mL portions of water
  8. dry with materialdried over MgSO4
  9. customEvaporation of the solvent in vacuo
  10. customafforded an oil, which

Sources & evidence

ORD record
ord-e9188651d20044c688ba4dea385e8efd
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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