Toluene → N-(p-acetylphenyl)acetamide

HRID 32469

Reaction equation

HRID 32469 reaction equation
NC1N(C2C=CC(OC)=CC=2)C(C2C=CC=C(NS(C)(=O)=O)C=2)[N:5]=[C:4]2[O:27]C=C[C:3]=12.C(O[C:34](=[O:36])[CH3:35])(=O)C.[C:37]1(C)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:4]([NH:5][C:37]1[CH:38]=[CH:39][C:40]([C:34](=[O:36])[CH3:35])=[CH:41][CH:42]=1)(=[O:27])[CH3:3]

Participants

4

Reactant 3

HCID 1140TolueneHCID 7918Acetic Anhydride2×HCID 178492023HCID 178492023, compound

Product 1

HCID 75937N-(p-acetylphenyl)acetamideYield 960%

Procedure

To a suspension of 4-aminoacetophenone 1 (74 g, 547 mmol) in toluene (700 mL), acetic anhydride (56 mL 593 mmol) was added dropwise at room temperature. Soon after added all of acetic anhydride, the reaction mixture became a clear solution and then rapidly began to make a white precipitation. The precipitation were filtrated and washed with a small amount of toluene then dried under reduced pressure to afford 2 as a white solid (93 g, 960% yield): MS(ES) m/e 178 [M+H].

Workup

  1. additionwas added dropwise at room temperature
  2. customa white precipitation
  3. customThe precipitation
  4. filtrationwere filtrated
  5. washwashed with a small amount of toluene
  6. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-9efe432e3cfc48a8b3a4a1bcd676ef47
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Linked notes

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