Sulfuric Acid → HCID 86732274, compound

HRID 930437Notes

Reaction equation

HRID 930437 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]1([CH3:20])[CH2:14][C@@H:13]([C:15]([F:18])([F:17])[F:16])[O:12][C:11]([NH2:19])=[N:10]1.S(=O)(=O)(O)O.[N+:26]([O-])([O-:28])=[O:27].[K+]>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:26]([O-:28])=[O:27])=[CH:4][C:3]=1[C@:9]1([CH3:20])[CH2:14][C@@H:13]([C:15]([F:18])([F:16])[F:17])[O:12][C:11]([NH2:19])=[N:10]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 86732273HCID 86732273, compound

Product 1

HCID 86732274HCID 86732274, compound

Procedure

To a solution of (4S,6S)-4-(2-chloro-3-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (1.06 g, 3.41 mmol) in sulfuric acid (13.64 ml, 256 mmol) cooled in an ice bath was added potassium nitrate (0.448 g, 4.44 mmol) in one portion. After stirred for 15 min, ice bath was removed, and the mixture was stirred at room temperature for 40 min. The reaction mixture was poured into ice water containing sodium carbonate (40 g). The resulted suspension was extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated and dried in vacuum to afford the crude (4S,6S)-4-(2-chloro-3-fluoro-5-nitrophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine as a light yellow solid, which was used in next step without purification. MS m/z=356 [M+H]+. Calculated for C12H10ClF4N3O3: 355.6.

Workup

  1. customice bath was removed
  2. stirringthe mixture was stirred at room temperature for 40 min
  3. additionThe reaction mixture was poured into ice water
  4. additioncontaining sodium carbonate (40 g)
  5. extractionThe resulted suspension was extracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customdried in vacuum

Sources & evidence

ORD record
ord-5956d85123af4bd9973a427278e73aec
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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