Acetone → N-(1-cycloheptylmethyl-2-pyrrolidinylmethyl)-2,3-dimethoxy-5-sulphamoyl benzamide

HRID 652778Notes

Reaction equation

HRID 652778 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:8][C:4]=1[C:5]([OH:7])=O.CC(C)=O.ClC(OCC)=O.[CH:28]1([CH2:35][N:36]2[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:41][NH2:42])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C(N(CC)CC)C.O>[CH:28]1([CH2:35][N:36]2[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:41][NH:42][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:10]=[C:11]([O:12][CH3:13])[C:3]=2[O:2][CH3:1])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 10928Ethyl chloroformateHCID 30176982,3-Dimethoxy-5-sulphamoylbenzoic acidHCID 542344271-Cycloheptylmethyl-2-aminomethylpyrrolidine

Product 1

HCID 53910372N-(1-cycloheptylmethyl-2-pyrrolidinylmethyl)-2,3-dimethoxy-5-sulphamoyl benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

13 g of 2,3-dimethoxy-5-sulphamoyl benzoic acid, 150 ml of acetone, 28 ml of water and 7 ml of triethylamine (density 0.726) are placed in a 250 ml flask fitted with an agitator, a thermometer, a condenser and a dropping funnel. The resultant solution is cooled from 0° to +5° C. 5.4 g of ethyl chloroformate is added drop by drop and the reaction medium is agitated for 45 minutes at room temperature and cooled to 0° C. again. 13.7 g of 1-cycloheptylmethyl-2-aminomethylpyrrolidine is added drop by drop. The medium is agitated for 1 hour at room temperature then left to stand. The crystals formed are drained, washed with water and dried in an oven at 30° C.

Workup

  1. customfitted with an agitator
  2. temperaturecooled to 0° C. again
  3. stirringThe medium is agitated for 1 hour at room temperature
  4. waitthen left
  5. customThe crystals formed
  6. washwashed with water
  7. customdried in an oven at 30° C.

Sources & evidence

ORD record
ord-2a555d57a26646dfb16cba25986c41a9
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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