Nitric Acid → HCID 66665493, compound

HRID 2196349Notes

Reaction equation

HRID 2196349 reaction equation
S(O)(O)(=O)=O.[F:6][CH:7]([F:22])[C@@:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:13][O:12][CH2:11][C:10]([NH2:14])=[N:9]1.[N+:23]([O-])([OH:25])=[O:24].N.O>OS(O)(=O)=O>[F:22][CH:7]([F:6])[C@@:8]1([C:15]2[CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=[CH:17][C:16]=2[F:21])[CH2:13][O:12][CH2:11][C:10]([NH2:14])=[N:9]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 12896473Azane;hydrateHCID 66665903HCID 66665903, compound

Product 1

HCID 66665493HCID 66665493, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of (R)-5-difluoromethyl-5-(2-fluoro-phenyl)-5,6-dihydro-2H-[1,4]oxazin-3-ylamine sulphate (127.2 g, 371.6 mmol) in conc. H2SO4 (380 mL) was added at 5-15° C. HNO3 (25.8 g, 408.8 mmol). After addition, the reaction mixture was added slowly to 12% NH3 water solution (2.6 L) at 10-20° C. The resulted suspension (pH˜8) was filtered to provide the title compound as a yellow solid: ESIMS: 290; [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 8.89 (m, 1H), 8.14 (m, 1H), 7.18 (dd, 1H), 6.10 (t, 1H), 5.65 (br s, 2H), 4.57 (dd, 1H), 4.13 (dd, 2H), 3.88 (m, 1H).

Workup

  1. additionAfter addition
  2. filtrationThe resulted suspension (pH˜8) was filtered

Sources & evidence

ORD record
ord-afa63d3ba0854dcd95960ee55a3993e0
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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