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

HRID 2285471Notes

Reaction equation

HRID 2285471 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-549b2e53485d45348099cd504f6ce067
Source dataset
uspto-grants-1982_04
Patent number
US04323503

Reaction notes

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