Sodium Carbonate → HCID 13556647, compound

HRID 280046Notes

Reaction equation

HRID 280046 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].C(=O)([O-])[O-].[Na+].[Na+].[Cl:18][CH2:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>C1(C)C(C)=CC=CC=1>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][S:22]([CH2:21][CH2:20][CH2:19][Cl:18])(=[O:24])=[O:23])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 154103-Chloropropanesulphonyl chlorideHCID 663013,5-Dimethoxyaniline

Product 1

HCID 13556647HCID 13556647, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3,5-Dimethoxyaniline (34.62 g, 0.226 mol) in xylene (500 mL) containing suspended sodium carbonate (12.0 g, 0.113 mol) was treated with 3-chloropropane sulfonyl chloride (40.0 g, 0.226 mol) added dropwise with stirring. Stirring was continued for twenty-four hours and the solvent was stripped to provide a black partially crystalline gum. Filtration through dry-column silica gel combined with crystallization from ethyl acetate/hexane provided N-(3,5-dimethoxyphenyl)-3-chloro-1-propanesulfonamide (20 g), m.p. 68°-71° C.

Workup

  1. additionadded dropwise
  2. stirringStirring
  3. waitwas continued for twenty-four hours
  4. customto provide a black partially crystalline gum
  5. filtrationFiltration through dry-column silica gel
  6. customcombined with crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e6d8fc22fe574fd48737aff510d5e1e7
Source dataset
uspto-grants-1986_05
Patent number
US04587360

Reaction notes

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