Dimethylformamide → 3-Acetylbenzamide

HRID 912037Notes

Reaction equation

HRID 912037 reaction equation
C[N:2]([CH:4]=[O:5])C.[C:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)C(O)=O)(=[O:8])[CH3:7].C(N(CC)CC)C.ClC(OCC)=O.[OH-].[NH4+]>>[C:6]([C:9]1[CH:17]=[C:16]([CH:15]=[CH:11][CH:10]=1)[C:4]([NH2:2])=[O:5])(=[O:8])[CH3:7]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 2203243-Acetylbenzoic acid

Product 1

HCID 232792313-Acetylbenzamide

Conditions

Temperature
0 °C

Procedure

General Procedure FF: Into DMF (11 ml, 140 mmol) solution of 3-acetylbenzoic acid (706 mg, 4.30 mmol) which was cooled in ice/water bath was added triethylamine (602 μl, 4.30 mmol) followed by addition of ethyl chloroformate (424 μl, 4.30 mmol) dropwise in 5 min under an atmosphere of nitrogen. The mixture was stirred at 0° C. for 30 min and then at rt for 30 min. Ammonium hydroxide (28% aq. solution; 1.15 ml) was added, and the mixture was stirred at rt for 3 h. After that time, the mixture was poured into ice/water, extracted with EtOAc (3×50 ml). The extracts were washed with water (2×30 ml), brine (30 ml), dried over MgSO4, filtered and concentrated in vacuo, giving the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ=2.66 (s, 3H), 7.58 (dt, J=0.4 & 8.0 Hz, 1H), 8.05 (md, J=8.0 Hz, 1H), 8.12 (md, J=8.0 Hz, 1H), 8.38-8.41 (m, 1H). MS (ES+): m/z 164.10 [MH+]. HPLC: tR=1.89 min (polar—5 min, ZQ3).

Workup

  1. waitat rt for 30 min
  2. stirringthe mixture was stirred at rt for 3 h
  3. extractionextracted with EtOAc (3×50 ml)
  4. washThe extracts were washed with water (2×30 ml), brine (30 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c16b0a430d94d2086c60b1a5389bd93
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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