Water → HCID 15036708, compound

HRID 2249135Notes

Reaction equation

HRID 2249135 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:22])[C:19]([OH:21])=O)=[CH:14][CH:13]=1)=[O:11].[CH:23]([NH2:26])([CH3:25])[CH3:24].O>O1CCCC1>[CH:23]([NH:26][C:19](=[O:21])[CH:18]([C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[NH:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])=[CH:17][CH:16]=1)[CH3:22])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 6363IsopropylamineHCID 15036706HCID 15036706, compound

Product 1

HCID 15036708HCID 15036708, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.38 g of 2-[4-(2,3-dichlorophenylcarbamoyl)phenyl]propionic acid was dissolved in 30 ml of anhydrous tetrahydrofuran. While cooling the solution with ice water, 2.43 g of N,N'-carbonyldiimidazole was added thereto, and the mixture was stirred for 30 minutes. Thereafter, 0.59 g of isopropylamine was added thereto. The mixture was returned to room temperature and stirred for 5 hours. After completion of the reaction, the reaction solution was poured into 200 ml of water, and the resulting crystals were collected by filtration, washed with water and dried, and then recrystallized from toluene to obtain 3.30 g of desired N-isopropyl-2-[4-(2,3-dichlorophenylcarbamoyl)-phenyl]-propionamide. The yield was 87%, and the melting point of this compound was from 203° to 204° C.

Workup

  1. additionwas added
  2. customwas returned to room temperature
  3. stirringstirred for 5 hours
  4. customAfter completion of the reaction
  5. filtrationthe resulting crystals were collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-51584bbf9182449bbb3f574367bc686f
Source dataset
uspto-grants-1991_08
Patent number
US05043006

Reaction notes

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