Hydrochloric Acid → HCID 86644107, compound

HRID 1959151Notes

Reaction equation

HRID 1959151 reaction equation
N([O-])=O.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]3[CH:18]=[CH:19][C:20](N)=[CH:21][C:16]=3[O:15][C:14]([CH3:24])([CH3:23])[N:13]=2)=[CH:8][CH:7]=1.[ClH:25].[S:26](=[O:28])=[O:27]>O.C(O)(=O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]3[CH:18]=[CH:19][C:20]([S:26]([Cl:25])(=[O:28])=[O:27])=[CH:21][C:16]=3[O:15][C:14]([CH3:24])([CH3:23])[N:13]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 23668193Sodium NitriteHCID 59442944HCID 59442944, compound

Product 1

HCID 86644107HCID 86644107, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (153 mg) in water (2.4 mL) was added dropwise to a solution of 4-fluorophenyl-2,2-dimethyl-2H-1,3-benzoxazin-7-amine (an objective compound of Reference Example 38(3); 600 mg) in acetic acid (18 mL) and concentrated hydrochloric acid (6 mL) at −5° C. and the mixture was stirred at the same temperature for one hour. To the reaction mixture was added a mixture of sulfur dioxide, acetic acid, cupric chloride and water at 0° C. and the mixture was stirred at the same temperature for one hour. The reaction mixture was poured into ice water (200 mL) and the mixture was extracted with ether (50 mL×3). The combined organic layer was washed successively with brine (50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL×2), dried over sodium sulfate and concentrated in vacuo to give the titled compound (400 mg) as a yellow oil, which was used in the next step without further purification.

Workup

  1. additionTo the reaction mixture was added
  2. extractionthe mixture was extracted with ether (50 mL×3)
  3. washThe combined organic layer was washed successively with brine (50 mL)
  4. dry with materiala saturated aqueous solution of sodium bicarbonate (50 mL×2), dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f91fced7ef248c180e03ce86a2bc76a
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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