1,2-Dichloroethane → Benzamide, N-(4-chlorophenyl)-

HRID 1945415Notes

Reaction equation

HRID 1945415 reaction equation
C12(C3C=CC(OCC(N[C:20]4[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=4)[C:23](O)=[O:24])=O)=CC=3)CC3CC(CC(C3)C1)C2.[Cl:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[Cl:31][C:32]1[CH:38]=[CH:37][C:35]([NH:36][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[CH:20][CH:21]=2)=[CH:34][CH:33]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 78124-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5124065HCID 5124065, compound

Product 1

HCID 96646Benzamide, N-(4-chlorophenyl)-Yield 132.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid (20 mg, 0.049 mmol), 4-chloro aniline (9.4 mg, 0.073 mmol) and DIPEA (9.56 mg, 0.073 mmol) in DMF (5 mL) was added EDC (14.18 mg, 0.073 mmol) and HOBt (9.99 mg, 0.073 mmol) at room temperature and continued stirring for 16 h at room temperature. Reaction mixture was diluted with ethyl acetate and sequentially washed with aqueous sodium bicarbonate, brine and water, and dried over MgSO4. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by column chromatography on silica gel (EtoAC:Hexane=1:5) to give 3-[2-adamantan-1-yl-phenoxy)-acetylamino]-N-(4-chloro-phenyl)-benzamide as a colorless crystals (15 mg, yield: 59%).

Workup

  1. customReaction mixture
  2. washsequentially washed with aqueous sodium bicarbonate, brine and water
  3. dry with materialdried over MgSO4
  4. filtrationThe solvent was filtered
  5. customevaporated under reduced pressure
  6. customto afford a crude solid, which
  7. customwas purified by column chromatography on silica gel (EtoAC:Hexane=1:5)

Sources & evidence

ORD record
ord-63b5322f5919430a847bdbb7e4f103fe
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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