6-Chloro-2h-1,3-benzoxazine-2,4(3h)-dione → 5-Cnac

HRID 855984Notes

Reaction equation

HRID 855984 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=O)[NH:8][C:7](=[O:12])[C:6]=2[CH:13]=1.C([O:16][C:17](=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]CBr)C>CC(N(C)C)=O>[Cl:1][C:2]1[CH:13]=[C:6]([C:7]([NH:8][CH2:9][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]([OH:26])=[O:16])=[O:12])[C:5]([OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 903596-Chloro-2h-1,3-benzoxazine-2,4(3h)-dioneHCID 264813Ethyl 8-bromooctanoate

Product 1

HCID 98398165-Cnac

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
45 °C

Procedure

222 L of dry dimethylacetamide is charged to a dry 200 gallon glass-lined reactor. The reactor agitator is set to 100–125 rpm. Cooling is applied to the condenser and valve reactor overheads are set for distillation. 41.6 kg of dry anhydrous sodium carbonate is charged to the reactor and the reactor charging port is closed. Caution is used due to some off-gassing and a slight exothermic reaction. 77.5 kg of dry 6-chloro-2H-1,3-benzoxazine-2,4(3H)-dione is charged to the reactor. Quickly, 88 kg of dry ethyl-8-bromooctanoate is charged to the reactor. The reaction is evacuated to 22–24 inches of vacuum and the reactor temperature is raised to 65–75° C. The reactor temperature is maintained and the contents are watched for foaming. The reactor mixture is sampled and monitored for conversion by monitoring for the disappearance of the bromo ester in the reaction mixture by gas chromatography. The reaction is complete after 7 hours. The vacuum is broken and the reactor contents are cooled to 45–50° C. The contents are centrifuged and the filtrate sent into a second 200 gallon glass-lined reactor. 119 L of ethanol (200 proof denatured with 0.5% toluene) is charged to the first 200 gallon reactor, warmed to about 45° C. and the filter cake washed with warm ethanol and this wash is charged to the reaction mixture in the second 200 gallon reactor.

Workup

  1. temperatureCooling
  2. distillationare set for distillation
  3. addition41.6 kg of dry anhydrous sodium carbonate is charged to the reactor
  4. customis closed
  5. customa slight exothermic reaction
  6. customThe reaction is evacuated to 22–24 inches of vacuum
  7. temperaturethe reactor temperature is raised to 65–75° C
  8. temperatureThe reactor temperature is maintained
  9. aliquotThe reactor mixture is sampled
  10. temperaturethe reactor contents are cooled to 45–50° C
  11. customthe filtrate sent into a second 200 gallon glass-lined reactor
  12. addition119 L of ethanol (200 proof denatured with 0.5% toluene) is charged to the first 200 gallon reactor
  13. washthe filter cake washed with warm ethanol
  14. additionthis wash is charged to the reaction mixture in the second 200 gallon reactor

Sources & evidence

ORD record
ord-1cd519f0dd6d4786ac176f6cf6d0c1b1
Source dataset
uspto-grants-2007_08
Patent number
US07262325B2

Reaction notes

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