Dimethylformamide → HCID 19008609, compound

HRID 1742188Notes

Reaction equation

HRID 1742188 reaction equation
[CH3:1]N(C=O)C.[Cl:6][C:7]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([Cl:35])[C:8]=1[O:9][C:10]1[CH:26]=[CH:25][C:13]2[NH:14][C:15](=[O:24])[C:16](C)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:17][C:12]=2[CH:11]=1.[H-].[Na+].Cl[CH:39]([F:41])[F:40]>O>[Cl:6][C:7]1([CH3:1])[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[C:27]([Cl:35])[CH:8]1[O:9][C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:39]([F:41])[F:40])[C:15](=[O:24])[CH:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:17][C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6372ChlorodifluoromethaneHCID 24758Sodium hydrideHCID 19008620HCID 19008620, compound2×

Product 1

HCID 19008609HCID 19008609, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF solution (50 ml) of ethyl 7-(2,6-dichloro-4-trifluoromethylphenoxy)-2-methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylate (Compound 3) (1.5 g) was added 60% sodium hydride (0.2 g), and the mixture was stirred for one hour. Then, while cooling in a dry ice-acetone bath, chlorodifluoromethane gas was introduced for one hour, and the mixture then stirred for 2 days and nights. Thereafter, water (50 ml) was added and the mixture was extracted twice with ethyl acetate (50 ml), and the extract was washed with water and then with saturated aqueous sodium chloride, and then dried over magnesium sulfate. The solvent was evaporated under a reduced pressure, and the residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=9/1) to give 0.6 g of the title compound (colorless oil).

Workup

  1. temperatureThen, while cooling in a dry ice-acetone bath
  2. stirringthe mixture then stirred for 2 days and nights
  3. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
  4. washthe extract was washed with water
  5. dry with materialwith saturated aqueous sodium chloride, and then dried over magnesium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-79973f04eb8f445bbc6541b08c4410b2
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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