Dimethylformamide → 4-Benzyl-3-butoxy-N,N-dimethyl-5-sulfamoylbenzamide

HRID 2082883Notes

Reaction equation

HRID 2082883 reaction equation
[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][C:9]=1[O:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:30][N:31](C)[CH:32]=O>>[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([N:31]([CH3:32])[CH3:30])=[O:13])=[CH:10][C:9]=1[O:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 537356464-Benzyl-3-n-butoxy-5-sulfamylbenzoic acid

Product 1

HCID 540414804-Benzyl-3-butoxy-N,N-dimethyl-5-sulfamoylbenzamide

Procedure

A mixture of 4-benzyl-3-n-butoxy-5-sulfamylbenzoic acid (3.6 g), thionyl chloride (20 ml) and N,N-dimethylformamide (0.1 ml) is refluxed for 1 hour and is then evaporated in vacuo. The resulting crude 4-benzyl-3-n-butoxy-5-sulfamylbenzoyl chloride is dissolved in methylene chloride (30 ml), and the resulting solution is during about 15 minutes added dropwise to a stirred mixture of dimethylamine (10 ml; 40% in water) and methylene chloride (20 ml), keeping the temperature at 0°-5° C. by external cooling. After stirring for an additional 2 hours at 22°-25° C., the mixture is washed with water and the organic layer is separated and dried in the presence of magnesium sulphate. Filtration followed by evaporation in vacuo yields crude 4-benzyl-3-n-butoxy-5-sulfamyl-N,N-dimethylbenzamide. After recrystallization from benzene it is obtained with a melting point of 199°-201° C.

Workup

  1. temperatureis refluxed for 1 hour
  2. customis then evaporated in vacuo
  3. dissolutionThe resulting crude 4-benzyl-3-n-butoxy-5-sulfamylbenzoyl chloride is dissolved in methylene chloride (30 ml)
  4. additionadded dropwise to a stirred mixture of dimethylamine (10 ml; 40% in water) and methylene chloride (20 ml)
  5. customat 0°-5° C.
  6. washthe mixture is washed with water
  7. customthe organic layer is separated
  8. dry with materialdried in the presence of magnesium sulphate
  9. filtrationFiltration
  10. customfollowed by evaporation in vacuo

Sources & evidence

ORD record
ord-87e01a984c3241c887c05551b6741de9
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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