Azane;hydrate → HCID 14347808, compound

HRID 2291762Notes

Reaction equation

HRID 2291762 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[C:12]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=[O:18])=O)C.O.[NH3:20]>C(O)C>[C:4]([CH2:6][N:7]1[C:12]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=[O:18])(=[O:3])[NH2:20]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 14347814HCID 14347814, compound

Product 1

HCID 14347808HCID 14347808, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-ethoxycarbonylmethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (1.27 g), ethanol (20 ml) and 28% ammonia water (10 g) was mixed at room temperature for 2 hours, and refluxed for 3 hours. After the solvent was concentrated, it was mixed with water, and filtered. Resulting product was washed with water and ethanol in that order, and recrystallized from methylisobutyl ketone to give the desired 4-carbamoylmethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (0.45 g). mp. 216.5°-219° C.

Workup

  1. additionwas mixed at room temperature for 2 hours
  2. temperaturerefluxed for 3 hours
  3. concentrationAfter the solvent was concentrated
  4. additionit was mixed with water
  5. filtrationfiltered
  6. washResulting product was washed with water and ethanol in that order
  7. customrecrystallized from methylisobutyl ketone

Sources & evidence

ORD record
ord-0028415454384410901017d78c6d7264
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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