2(3H)-Benzoxazolone → HCID 82254802, compound

HRID 1619931Notes

Reaction equation

HRID 1619931 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[Cl:11][CH:12]([CH2:16][CH3:17])[C:13](O)=[O:14]>>[Cl:11][CH:12]([CH2:16][CH3:17])[C:13]([C:7]1[CH:8]=[CH:9][C:4]2[NH:3][C:2](=[O:10])[O:1][C:5]=2[CH:6]=1)=[O:14]

Participants

3

Reactant 2

HCID 60432(3H)-BenzoxazoloneHCID 201372-Chlorobutyric acid

Product 1

HCID 82254802HCID 82254802, compound

Conditions

Temperature
125 °C

Procedure

81.70 g (604.65 mmol) 2-benzoxazolinone are stirred together with 720.00 g polyphosphoric acid at 80° C. 63 mL (607.64 mmol) 2-chlorobutyric acid are added and the mixture is stirred for 3 h at 125° C. The reaction mixture is then poured onto ice water and extracted with DCM. The org. phase is concentrated by rotary evaporation i. V. and the residue is separated on silica gel (eluant cyclohexane/EA). The suitable fractions are concentrated by rotary evaporation i. V. and the residue is crystallised with diethyl ether.

Workup

  1. additionThe reaction mixture is then poured onto ice water
  2. extractionextracted with DCM
  3. concentrationphase is concentrated by rotary evaporation i
  4. customand the residue is separated on silica gel (eluant cyclohexane/EA)
  5. concentrationThe suitable fractions are concentrated by rotary evaporation i
  6. customand the residue is crystallised with diethyl ether

Sources & evidence

ORD record
ord-0ca281d4a5c04ce091b478f001196831
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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