Acetic Anhydride → HCID 68700315, compound

HRID 2244379Notes

Reaction equation

HRID 2244379 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:3]=1[C:4]([N:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=[O:5].[C:35](OC(=O)C)(=[O:37])[CH3:36].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[C:35]([NH:1][C:2]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:3]=1[C:4]([N:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)=[O:5])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 81531DiisopropylethylamineHCID 68699354HCID 68699354, compound

Product 1

HCID 68700315HCID 68700315, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-N-(4-tert-butyl-benzyl)-5-chloro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (140 mg, 0.286 mmol) was dissolved in methylene chloride (2 ml). Acetic acid anhydride (32 mg, 0.315 mmol) and ethyl-diisopropylamine (41 mg, 0.315 mmol) were added and the reaction was stirred over night at RT. Further acetic acid anhydride (30 μl) was added and the reaction was stirred for another night at RT. The reaction was extracted with ethyl acetate, the combined organic layers were concentrated in vacuo and the residue was purified by flash column chromatography (heptane/ethyl acetate:7/3) to yield the desired product (110 mg, 72%) as an off-white solid. MS (ISP) 529.2 (M−H)−.

Workup

  1. stirringthe reaction was stirred for another night at RT
  2. extractionThe reaction was extracted with ethyl acetate
  3. concentrationthe combined organic layers were concentrated in vacuo
  4. customthe residue was purified by flash column chromatography (heptane/ethyl acetate:7/3)

Sources & evidence

ORD record
ord-391d016684854884b108f15529978a07
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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