Chloroform → N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide

HRID 2285475Notes

Reaction equation

HRID 2285475 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH2:10])[CH:2]=[CH2:3].C(Cl)(Cl)Cl.[CH3:15][NH:16][S:17]([C:20]1[CH:21]=[C:22]([C:30](Cl)=[O:31])[C:23]2[O:28][CH2:27][CH2:26][O:25][C:24]=2[CH:29]=1)(=[O:19])=[O:18]>O>[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH:10][C:30]([C:22]1[C:23]2[O:28][CH2:27][CH2:26][O:25][C:24]=2[CH:29]=[C:20]([S:17](=[O:19])(=[O:18])[NH:16][CH3:15])[CH:21]=1)=[O:31])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 1172961-(Allyl)pyrrolidine-2-methylamineHCID 205447207-Methylsulfamoyl-1,4-benzodioxane-5-carbonyl chloride

Product 1

HCID 24834937N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamideYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

85 g of levorotatory 1-allyl-2-aminomethyl-pyrrolidine, 610 cm3 of chloroform, and gradually, 178 g of 7-methylsulfamoyl-1,4-benzodioxane-5-carbonyl chloride at a temperature of from 5°-10° C. were introduced into a balloon flask provided with an agitator and a thermometer. After agitation of the mixture 1.2 liters of water were added and then chloroform was distilled. The remaining solution was filtered and then the base was precipitated with 70 cm3 of 20% ammonia. The crystals formed were dried off and washed with water. After recrystallization from ethyl acetate, 117 g of levorotatory-N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide was produced (M.P.: 101°-102° C.; yield: 49%).

Workup

  1. customprovided with an agitator
  2. distillationchloroform was distilled
  3. filtrationThe remaining solution was filtered
  4. customthe base was precipitated with 70 cm3 of 20% ammonia
  5. customThe crystals formed
  6. customwere dried off
  7. washwashed with water
  8. customAfter recrystallization from ethyl acetate, 117 g of levorotatory-N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide
  9. customwas produced (M.P.: 101°-102° C.; yield: 49%)

Sources & evidence

ORD record
ord-0f464aa2c7374ac9b57a76e500881f62
Source dataset
uspto-grants-1982_04
Patent number
US04323503

Reaction notes

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