Carzenide → Benzamide, 4-(aminosulfonyl)-N-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-

HRID 703533Notes

Reaction equation

HRID 703533 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.S(C1C=CC(CCl)=CC=1)(=O)(=O)N.[S:27]([C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)(=[O:30])(=[O:29])[NH2:28].S(Cl)(Cl)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:11][C:35](=[O:36])[C:34]2[CH:38]=[CH:39][C:31]([S:27](=[O:30])(=[O:29])[NH2:28])=[CH:32][CH:33]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 8739CarzenideHCID 24386Thionyl ChlorideHCID 88349p-(2-(Dimethylamino)ethoxy)benzylamineHCID 223818924-Sulfamoylbenzyl chloride

Product 1

HCID 3078819Benzamide, 4-(aminosulfonyl)-N-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-Yield 40.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a cooled solution of 1.50 g of 4-[2-(dimethylamino)ethoxy]benzylamine and 0.87 g of triethylamine in 10 ml of chloroform was added 1.87 g of 4-sulfamoylbenzyl chloride, which was prepared from 1.71 g of 4-sulfamoylbenzoic acid with 16.3 g of thionyl chloride in the usual way, with stirring. The mixture was stirred at room temperature for 30 minutes and the solvent was evaporated. Hydrochloric acid (10%) was added to the residue and the aqueous solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate and was extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue was washed with ethyl acetate to give 1.19 g of pale yellow crystals, which were recrystallized from ethanol to give colorless crystals, m.p. 173.5°-174.5° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. customthe solvent was evaporated
  3. additionHydrochloric acid (10%) was added to the residue
  4. washthe aqueous solution was washed with ethyl acetate
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated
  9. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-1f1b01e050b7483097e4b70fad8fc3b7
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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