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

HRID 127413Notes

Reaction equation

HRID 127413 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-2e13bbeeda4e4c1591186c2292fd1fa7
Source dataset
uspto-grants-1981_03
Patent number
US04255580

Reaction notes

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