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

HRID 2185144Notes

Reaction equation

HRID 2185144 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
70 °C

Procedure

222 L of dry dimethylacetamide was charged to a dry 200 gallon glass-lined reactor. The reactor agitator was set to 100-125 rpm. Cooling was applied to the condenser and valve reactor overheads were set for distillation. 41.6 kg of dry anhydrous sodium carbonate was charged to the reactor and the reactor charging port was closed. Caution was 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 was charged to the reactor. Quickly, 88 kg of dry ethyl-8-bromooctanoate was charged to the reactor. The reaction was evacuated to 22-24 inches of vacuum and the reactor temperature was raised to 65-75° C. The reactor temperature was maintained and the contents were watched for foaming. The reactor mixture was sampled and monitored for conversion by monitoring for the disappearance of the bromo ester in the reaction mixture by gas chromatography. The reaction was complete (0.6% bromo ester was found) after 7 hours. The vacuum was broken and the reactor contents cooled to 45-50° C. The contents were centrifuged and the filtrate sent into a second 200 gallon glass-lined reactor. 119 L of ethanol (200 proof denatured with 0.5% toluene) was charged to the first 200 gallon reactor, wanned to about 45° C. and the filter cake washed with warm ethanol and this wash was charged to the reaction mixture in the second 200 gallon reactor.

Workup

  1. temperatureCooling
  2. distillationwere set for distillation
  3. addition41.6 kg of dry anhydrous sodium carbonate was charged to the reactor
  4. customwas closed
  5. customa slight exothermic reaction
  6. customThe reaction was evacuated to 22-24 inches of vacuum
  7. temperatureThe reactor temperature was maintained
  8. aliquotThe reactor mixture was sampled
  9. customafter 7 hours
  10. temperaturethe reactor contents 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) was charged to the first 200 gallon reactor
  13. customwanned to about 45° C.
  14. washthe filter cake washed with warm ethanol
  15. additionthis wash was charged to the reaction mixture in the second 200 gallon reactor

Sources & evidence

ORD record
ord-d43c05afa3ad4911a9b93807a50cf15f
Source dataset
uspto-grants-2002_06
Patent number
US06399798B2

Reaction notes

Loading…