Hydrochloric Acid → 5-Acetyl-1,3-benzoxazol-2(3H)-one

HRID 132679Notes

Reaction equation

HRID 132679 reaction equation
C(N(CC)CC)C.ClC(Cl)(O[C:12](=[O:18])[O:13][C:14](Cl)(Cl)Cl)Cl.[NH2:20][C:21]1[CH:26]=[C:25]([C:27]([CH3:29])=[O:28])[CH:24]=[CH:23]C=1O.Cl>C1COCC1>[CH3:29][C:27]([C:25]1[CH:24]=[CH:23][C:14]2[O:13][C:12](=[O:18])[NH:20][C:21]=2[CH:26]=1)=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 94429TriphosgeneHCID 137241423'-Amino-4'-hydroxyacetophenone

Product 1

HCID 151135715-Acetyl-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.8 ml of triethylamine and 2.75 g (0.0093 mol) of triphosgene are added to a mixture of 4.2 g (0.0277 mol) of 2-amino-4-methylcarbonylphenol in 100 ml of THF, at 0° C. The mixture is stirred at room temperature for 1 hour, poured into 100 ml of a 0.5N HCl solution and extracted with ethyl acetate, the organic phase is dried and the solvent is evaporated off. The compound of the title is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is dried
  3. customthe solvent is evaporated off
  4. customThe compound of the title is obtained

Sources & evidence

ORD record
ord-4bcf49dca56c44ff98bc5112ba8c17d6
Source dataset
uspto-grants-2008_06
Patent number
US07388031B2

Reaction notes

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