Ammonia → 5-Difluoromethyl-5-(2-fluoro-phenyl)-2,2-dimethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

HRID 81585Notes

Reaction equation

HRID 81585 reaction equation
[F:1][CH:2]([F:19])[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[NH:8][C:7](=S)[C:6]([CH3:11])([CH3:10])[O:5][CH2:4]1.CO.[NH3:22]>>[F:1][CH:2]([F:19])[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:4][O:5][C:6]([CH3:11])([CH3:10])[C:7]([NH2:22])=[N:8]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86650268HCID 86650268, compound

Product 1

HCID 666659215-Difluoromethyl-5-(2-fluoro-phenyl)-2,2-dimethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

Conditions

Temperature
80 °C

Procedure

5-Difluoromethyl-5-(2-fluoro-phenyl)-2,2-dimethyl-morpholine-3-thione (2.50 g, 8.64 mmol) was dissolved in NH3 solution 7 mol/L in methanol (40.7 mL, 285 mmol). The sealed reaction vessel was heated to 80° C. for 7 h, then the temperature was lowered to 70° C. and the reaction mixture was stirred over night. The reaction mixture was evaporated and purified on a silica gel column by eluting with CH2Cl2/1-4% EtOH:NH3 9:1 to give 2.09 g of the title compound as an off-white solid.

Workup

  1. customThe sealed reaction vessel
  2. customwas lowered to 70° C.
  3. customThe reaction mixture was evaporated
  4. custompurified on a silica gel column
  5. washby eluting with CH2Cl2/1-4% EtOH:NH3 9:1

Sources & evidence

ORD record
ord-fb9dd1e678324dfa9dd76482eb45ec22
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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