Hydrochloric Acid → HCID 86626313, compound

HRID 1929417Notes

Reaction equation

HRID 1929417 reaction equation
N[C:2]1[CH:21]=[CH:20][C:5]2[N:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1.[ClH:22].N([O-])=O.[Na+].[S:27]([O-:30])(O)=[O:28].[Na+]>C(O)(=O)C.O.[Cu](Cl)Cl>[F:19][C:16]1[CH:17]=[CH:18][C:13]([N:6]2[C:5]3[CH:20]=[CH:21][C:2]([S:27]([Cl:22])(=[O:30])=[O:28])=[CH:3][C:4]=3[O:9][C:8]([CH3:11])([CH3:10])[C:7]2=[O:12])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 23665763Sodium BisulfiteHCID 23668193Sodium NitriteHCID 66790534HCID 66790534, compound

Product 1

HCID 86626313HCID 86626313, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 7-amino-4-(4-fluorophenyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 15, 50 mg) in acetic acid (465 μL)/concentrated hydrochloric acid (570 μL) was added a solution of sodium nitrite (13.3 mg) in water (115 μL) under ice-cooling, and the mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture was added a mixture of sodium hydrogen sulfite (182 mg), copper(II) chloride (23.5 mg), acetic acid (225 μL) and concentrated hydrochloric acid (115 μL) at the same temperature, and the mixture was stirred at room temperature for 2 hours. After ice-cooling, the reaction mixture was gradually poured to water with ice (15 mL) and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated in vacuo to give crude 4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-sulfonyl chloride.

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture was added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. temperatureAfter ice-cooling
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e8511d2bdbb4c6cb46fd1df21cb7b2b
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

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