3,4-Dichloroaniline → N-(3,4-dichlorophenyl)-2-(3-hydroxyphenyl)acetamide

HRID 2114720Notes

Reaction equation

HRID 2114720 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:35][C:36]1[CH:37]=[C:38]([CH:40]=[CH:41][C:42]=1[Cl:43])[NH2:39]>CN(C=O)C>[Cl:35][C:36]1[CH:37]=[C:38]([NH:39][C:9](=[O:11])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)[CH:40]=[CH:41][C:42]=1[Cl:43]

Participants

6

Reactant 4

HCID 72573,4-DichloroanilineHCID 121223'-Hydroxyphenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 23440791N-(3,4-dichlorophenyl)-2-(3-hydroxyphenyl)acetamideYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxyphenyl acetic acid (5.0 g, 0.03 mol) in DMF (50 ml) was added 1-hydroxybenzotriazole hydrate (4.86 g, 0.03 mol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (6.9 g, 0.036 mol). To the flask was added 3,4-dichloroaniline (4.86 g, 0.03 mol). The reaction was allowed to stir overnight. Solvent was removed and the reaction was diluted with ethyl acetate. The reaction mixture was washed with 1N HCl, 10% sodium carbonate solution, and brine. The organic layer was dried over MgSO4, filtered and concentrated to provide the title compound (5.5 g, 62% yield): ES-MS (m/z) 296 [M+H]+.

Workup

  1. customSolvent was removed
  2. additionthe reaction was diluted with ethyl acetate
  3. washThe reaction mixture was washed with 1N HCl, 10% sodium carbonate solution, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-868e27beb28649efbb097b05a371b1bd
Source dataset
uspto-grants-2008_10
Patent number
US07435729B2

Reaction notes

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