1,2-Dichloroethane → Benzamide

HRID 1945416Notes

Reaction equation

HRID 1945416 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.FC(F)(F)C1C=C([NH2:39])C=CC=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:23]([NH2:39])(=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 73753-(Trifluoromethyl)anilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5124065HCID 5124065, compound

Product 1

HCID 2331BenzamideYield 248.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid (50.0 mg, 0.13 mmol), 3-trifluoromethyl-phenylamine (31.5 mg, 0.03 ml 0.20 mmol), EDC (37.4 mg, 0.20 mmol) and HOBt (30.0 mg, 0.20 mmol) in DMF 1.3 mL was added DIPEA (0.04 ml, 0.20 mmol). Reaction mixture was stirred, and separated by ethyl acetate and 10% HCl. It was sequentially washed with 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 silica gel flash column chromatography (EtoAC:Hexane=1:3) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-3-trifluoromethyl-phenyl)-benzamide as a white solid (39.1 mg, 54.9% yield).

Workup

  1. customReaction mixture
  2. customseparated by ethyl acetate and 10% HCl
  3. washIt was sequentially washed with brine and water
  4. dry with materialdried over MgSO4
  5. filtrationThe solvent was filtered
  6. customevaporated under reduced pressure
  7. customto afford a crude solid, which
  8. customwas purified by silica gel flash column chromatography (EtoAC:Hexane=1:3)

Sources & evidence

ORD record
ord-717f45f708eb44ee8b2ce3e117f56393
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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