2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one → HCID 15766706, compound

HRID 1707592Notes

Reaction equation

HRID 1707592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[NH:10][NH2:11])=[CH:4][CH:3]=1.[F:13][C:14]([F:27])([F:26])[C:15]1[O:20][C:19](=O)[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[N:16]=1>N1C=CC=CC=1.ClCCl.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:10][N:11]2[C:19](=[O:20])[C:18]3[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:16]=[C:15]2[C:14]([F:13])([F:26])[F:27])=[O:12])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 9148992-(trifluoromethyl)-4H-3,1-benzoxazin-4-oneHCID 27578593-amino-1-(4-chlorophenyl)urea

Product 1

HCID 15766706HCID 15766706, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

4-(p-Chlorophenyl)semicarbazide (1.49 g, 8.03 mmol) is added to a solution of 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (1.72 g, 8.00 mmol) in pyridine (27 mL) at 100° C. The reaction mixture is stirred for 15 hours at 100° C., cooled to room temperature and concentrated in vacuo to obtain a solid. The solid is diluted with dichloromethane and the mixture is washed sequentially with 10% hydrochloric acid and water and concentrated in vacuo to obtain a tan solid. The tan solid is washed with dichloromethane and filtered. The filtrate is concentrated in vacuo to obtain a brown foam. The foam is diluted with ether and the mixture is washed sequentially with 10% hydrochloric acid, water and saturated sodium hydrogen carbonate solution, dried over anhydrous MgSO4, decolorized with carbon and concentrated in vacuo to obtain a cream colored foam. Flash chromatography of the cream colored foam using silica gel and a 3:1 dichloromethane/hexanes solution gives the title product as a white solid, 0.36 g, which is identified by 1HNMR spectral analysis.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto obtain a solid
  4. washthe mixture is washed sequentially with 10% hydrochloric acid and water
  5. concentrationconcentrated in vacuo
  6. customto obtain a tan solid
  7. washThe tan solid is washed with dichloromethane
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated in vacuo
  10. customto obtain a brown foam
  11. washthe mixture is washed sequentially with 10% hydrochloric acid, water and saturated sodium hydrogen carbonate solution
  12. dry with materialdried over anhydrous MgSO4
  13. concentrationconcentrated in vacuo
  14. customto obtain a cream colored foam

Sources & evidence

ORD record
ord-826c53947a2c491db51452616f97def8
Source dataset
uspto-grants-1994_10
Patent number
US05354755

Reaction notes

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