p-Anisoyl chloride → HCID 3509429, compound
Reaction equation
N[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].CC[N:13](CC)CC.[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>C1COCC1>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:13][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)(=[O:4])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 2-amino acetophenone (1.0 g, 7.39 mmol), THF (15 mL) and Et3N (2.39 g, 23.64 mmol). To the solution p-methoxy benzoyl chloride (1.32 g, 7.76 mmol) in THF (15 mL) was added slowly at 0° C. and stirred for 30 min at 0° C. Then the reaction mixture was stirred for 24 h at rt under nitrogen. The reaction mixture was poured into ice water. The crude product was collected and crude product was purified by column chromatography using 25% EtOAc in hexane to give 1.865 g of N-(2-acetylphenyl)-4-methoxybenzamide (93%).
Workup
- customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
- stirringThen the reaction mixture was stirred for 24 h at rt under nitrogen
- customThe crude product was collected
- customcrude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-61e5580952e044ababf5fcd5805d782a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242130B2
Reaction notes
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