Water → HCID 21829905, compound

HRID 1600545Notes

Reaction equation

HRID 1600545 reaction equation
[Br:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([NH:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=O)=[O:4].Cl.CN(CCCN=C=NCC)C.[Cl:30][C:31]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:32]=1[NH2:33].O>ClCCl>[Cl:30][C:31]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:32]=1[NH:33][C:7](=[O:9])[C:6]([NH:5][C:3](=[O:4])[CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[Br:1])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 72622,5-DichloroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21829923HCID 21829923, compound

Product 1

HCID 21829905HCID 21829905, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(α-bromophenylacetylamino)isobutyric acid (1.9 g) in dichloromethane (30 mL) was cooled to 0° C., to which dimethylaminopropylethylcarbodiimide hydrochloride (1.3 g) was added. The mixture was stirred for 10 minutes at 0° C. to room temperature. 2,5-Dichloroaniline (1.0 g) was added to the mixture, which was stirred overnight at room temperature. The reaction solution was poured into water and the mixture was extracted with chloroform. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent, 2.3 g of N-(2,5-dichlorophenyl)-2-(α-bromophenylacetylamino)isobutyramide was obtained as viscous liquid.

Workup

  1. additionwas added
  2. stirringwas stirred overnight at room temperature
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-b83bb2fc6aad43af87d3340b85e11f40
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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