Chloroform → N-(1-cyclohexyl-3-pyrrolidyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide

HRID 1660001Notes

Reaction equation

HRID 1660001 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)Cl.[CH3:17][NH:18][S:19]([C:22]1[CH:23]=[C:24]([C:32](Cl)=[O:33])[C:25]2[O:30][CH2:29][CH2:28][O:27][C:26]=2[CH:31]=1)(=[O:21])=[O:20]>C(O)(=O)C.O>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([NH:12][C:32]([C:24]3[C:25]4[O:30][CH2:29][CH2:28][O:27][C:26]=4[CH:31]=[C:22]([S:19](=[O:21])(=[O:20])[NH:18][CH3:17])[CH:23]=3)=[O:33])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 36700741-Cyclohexylpyrrolidin-3-amineHCID 205447207-Methylsulfamoyl-1,4-benzodioxane-5-carbonyl chloride

Product 1

HCID 24834928N-(1-cyclohexyl-3-pyrrolidyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamideYield 61.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

84 g of 1-cyclohexyl-3-aminopyrrolidine, 430 ml of chloroform and 146 g of 7-methylsulfamoyl-1,4-benzodioxane-5-carbonyl chloride were introduced into a balloon flask provided with an agitator and a thermometer. After agitation of the mixture, the base was extracted with methylene chloride and then the solvent was evaporated. The crystals formed were dissolved in boiling absolute alcohol and the resulting solution was filtered on carbon black. The crystals produced after cooling were dissolved in a solution of acetic acid in water and then the solution was filtered over carbon black and the base was reprecipitated by the addition of 20% ammonia. 129.5 g of N-(1-cyclohexyl-3-pyrrolidyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide was produced (M.P.: 160°-161° C.; yield: 61.2%).

Workup

  1. customprovided with an agitator
  2. extractionAfter agitation of the mixture, the base was extracted with methylene chloride
  3. customthe solvent was evaporated
  4. customThe crystals formed
  5. dissolutionwere dissolved
  6. filtrationthe resulting solution was filtered on carbon black
  7. customThe crystals produced
  8. temperatureafter cooling
  9. filtrationthe solution was filtered over carbon black
  10. customthe base was reprecipitated by the addition of 20% ammonia

Sources & evidence

ORD record
ord-a4d9c8b5129b4f918f9edae591247f22
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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