Ammonia → 4-Acetylbenzamide

HRID 10714Notes

Reaction equation

HRID 10714 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)([N:15]1C=CN=C1)=O.N>O1CCCC1>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:15])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 114704-Acetylbenzoic AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 111594974-AcetylbenzamideYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ex-92A: To a solution of 4-acetyl-benzoic acid (0.5 g, 3.05 mmol) in tetrahydrofuran (10 mL) was added carbonyldiimidazole (0.74 g, 4.75 mmol). The solution was allowed to stir at ambient temperature for one hour and cooled to 0° C. followed by addition of ammonia (28% in water, 3 mL, 21 mmol). The solution was continued to stir at 0° C. for another one hour. The solvent was removed under reduced pressure. The residue was treated with water, filtered, washed with water, dried in vacuo to give 4-acetyl-benzamide (0.25 g, 50%) as a white solid. 1H NMR (DMSO-d6) δ 8.11 (bs, 1H), 8.00 (d, J=9 Hz, 2H), 7.95 (d, J=9 Hz, 2H), 7.53 (bs, 1H), 2.59 (s, 3H).

Workup

  1. temperaturecooled to 0° C.
  2. stirringto stir at 0° C. for another one hour
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was treated with water
  5. filtrationfiltered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-06f80710ee084514bbedbcbd6a4d584a
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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