Hydrochloric Acid → 2-acetoxy-5-chloro-N-({[3,5-bis(trifluoromethyl)phenyl]carbamoyl)methyl)benzamide

HRID 644452

Reaction equation

HRID 644452 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([O:16][C:17]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:18]=1[C:19]([OH:21])=O)(=[O:15])[CH3:14].Cl.[NH2:28][CH2:29][C:30]([NH:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=1)=[O:31].ON1C2C=CC=CC=2N=N1.Cl>CN(C)C=O>[C:13]([O:16][C:17]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:18]=1[C:19]([NH:28][CH2:29][C:30](=[O:31])[NH:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:44])([F:45])[F:46])[CH:34]=1)=[O:21])(=[O:15])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28208132-(Acetyloxy)-5-chlorobenzoic acidHCID 574592632-amino-N-[3,5-bis(trifluoromethyl)phenyl]acetamide hydrochloride

Product 1

HCID 230699552-acetoxy-5-chloro-N-({[3,5-bis(trifluoromethyl)phenyl]carbamoyl)methyl)benzamideYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC.HCl (95.9 mg, 0.5 mmol) was added to a solution of 2-acetoxy-5-chlorobenzoic acid (59.1 mg, 0.28 mmol), 2-amino-N-[3,5-bis(trifluoromethyl)phenyl]acetamide hydrochloride (80.8 mg, 0.25 mmol) and 1-hydroxybenzotriazole (37.2 mg, 0.28 mmol) in N,N-dimethylformamide (3 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2→1:1) to give the title compound (83.7 mg, 69.3%) as a white crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2→1:1)

Sources & evidence

ORD record
ord-ebf4a2408dec4108a5d720d6086f8553
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Linked notes

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