1,1'-Carbonyldiimidazole → N-(1-ethyl-2-pyrrolidylmethyl)-7-ethylsulfonyl-1,4-benzodioxane-5-carboxamide

HRID 2052628Notes

Reaction equation

HRID 2052628 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:16]([OH:18])=O)[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:15]=1)(=[O:5])=[O:4])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[CH2:38][NH2:39])[CH3:32]>O1CCCC1>[CH2:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[CH2:38][NH:39][C:16]([C:8]1[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:15]=[C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH:7]=1)=[O:18])[CH3:32]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 205447587-Ethylsulfonyl-1,4-benzodioxane-5-carboxylic acid

Product 1

HCID 20293650N-(1-ethyl-2-pyrrolidylmethyl)-7-ethylsulfonyl-1,4-benzodioxane-5-carboxamideYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13 g of 7-ethylsulfonyl-1,4-benzodioxane-5-carboxylic acid, 300 ml of tetrahydrofuran and 13 g of carbonyldiimidazole were introduced into a balloon flask provided with an agitator, a thermometer and a condenser. The mixture was agitated at ambient temperature and then 9.5 g of 1-ethyl-2-aminomethylpyrrolidine was added. Agitation was maintained at ambient temperature and then the solvent was evaporated under vacuum. The crystals produced were washed with water and then dried. 14 g of N-(1-ethyl-2-pyrrolidylmethyl)-7-ethylsulfonyl-1,4-benzodioxane-5-carboxamide was produced (M.P.: 118°-119° C.; yield: 73.8%)

Workup

  1. customprovided with an agitator
  2. temperatureAgitation was maintained at ambient temperature
  3. customthe solvent was evaporated under vacuum
  4. customThe crystals produced
  5. washwere washed with water
  6. customdried

Sources & evidence

ORD record
ord-a7393dc98f374edeb6bcad06e328301e
Source dataset
uspto-grants-1980_01
Patent number
US04186135

Reaction notes

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