Dimethylformamide → HCID 14771558, compound

HRID 329718Notes

Reaction equation

HRID 329718 reaction equation
Br[C:2]([CH3:19])([CH3:18])[C:3]([NH:5][C:6]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=1[OH:17])=[O:4].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:16][C:14]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]2[O:17][C:2]([CH3:19])([CH3:18])[C:3](=[O:4])[NH:5][C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14771578HCID 14771578, compound

Product 1

HCID 14771558HCID 14771558, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7.0 g of methyl 3-(2-bromo-2-methylpropionylamino)-5-chlorosalicylate, 3.6 g of potassium carbonate and 70 ml of dimethylformamide is stirred at 80° C. for 4 hours. After cooling, the resultant solution is poured into water and extracted with chloroform. The extract is washed with water and dried over magnesium sulfate followed by distillation of the solvent under reduced pressure to give 4.2 g of methyl 6-chloro-3,4-dihydro-2,2-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate, melting at 178°-179° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationfollowed by distillation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b27795aa75ed47ef859f9b35c17f9249
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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