Water → HCID 15036708, compound

HRID 483907Notes

Reaction equation

HRID 483907 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-67e9f85aaae5477b9e003e5fd9faa5e7
Source dataset
uspto-grants-1993_07
Patent number
US05227511

Reaction notes

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