Water → HCID 19008614, compound

HRID 1742191Notes

Reaction equation

HRID 1742191 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH3:18])[C:10](=[O:17])[C:11]([CH3:16])([C:13]([OH:15])=[O:14])[O:12][C:7]=2[CH:6]=1.C1(NC2CCCCC2)CCCCC1.Br[CH2:43][C:44]([O:46][CH3:47])=[O:45].O>CN(C=O)C>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH3:18])[C:10](=[O:17])[C:11]([CH3:16])([C:13]([O:15][CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:14])[O:12][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7582DicyclohexylamineHCID 60984Methyl bromoacetateHCID 19008591HCID 19008591, compound2×

Product 1

HCID 19008614HCID 19008614, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

7-(2-Chloro-4-trifluoromethylphenoxy)-2,4-dimethyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid (Compound 23) (0.4 g) was dissolved in DMF (0.2 ml) and dicyclohexylamine (0.2 ml) was added thereto, followed by stirring at 60° C. for 15 minutes. Then methyl bromoacetate (0.2 g) was added, the mixture further stirred at 60° C. for 3 hours, to the reaction mixture was added water (20 ml), and the mixture was extracted twice with ethyl acetate (20 ml). The extract was washed with water and then with saturated aqueous sodium chloride, and then dried over magnesium sulfate, followed by an evaporation of the solvent under a reduced pressure. The residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1) to give 0.3 g of the title compound (colorless crystals).

Workup

  1. stirringthe mixture further stirred at 60° C. for 3 hours, to the reaction mixture
  2. extractionthe mixture was extracted twice with ethyl acetate (20 ml)
  3. washThe extract was washed with water
  4. dry with materialwith saturated aqueous sodium chloride, and then dried over magnesium sulfate
  5. customfollowed by an evaporation of the solvent under a reduced pressure
  6. customThe residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7bda6d6ffd494f74bde421b8416f2385
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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