HCID 22394176, compound → HCID 23349430, compound

HRID 261137Notes

Reaction equation

HRID 261137 reaction equation
Br.[Br:2][CH2:3][C:4]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=1[NH2:6].[C:12](Cl)(Cl)=[O:13].C1C=CC=CC=1>C1C=CC=CC=1>[Br:2][CH2:3][C:4]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=1[N:6]=[C:12]=[O:13]

Participants

4

Reactant 2

HCID 22394176HCID 22394176, compoundHCID 86736609HCID 86736609, compound

Product 1

HCID 23349430HCID 23349430, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.32 g of 2-bromomethyl-5-chloroaniline hydrobromide is added to 30 ml of benzene containing 12.5% phosgene (w/v) and the mixture refluxed in a vessel equipped with a Dean-Stark trap and additional phosgene/benzene added for a total of 250 ml (over a period of 6 hrs; 1/2 ml of water collected in the trap). The reaction mixture is cooled to 20°, insolubles removed by filtration and the filtrate concentrated (solvent removed), then distilled under vacuum to obtain 2-bromomethyl-5-chlorophenylisocyanate (distills at 0.05 mm Hg/50°). Further distillation yields 2-bromomethyl 4-bromo-5-chlorophenyl isocyanate (which may be refined by crystallization from petroleum ether, m.p. 48°-50°) which is useful as an intermediate in Examples 4 and 5 in preparing 6-bromo-7-chloro-4H-1,3-benzoxazine analogs of the title product of this example.

Workup

  1. temperaturethe mixture refluxed in a vessel
  2. additionadded for a total of 250 ml (over a period of 6 hrs
  3. custom1/2 ml of water collected in the trap)
  4. temperatureThe reaction mixture is cooled to 20°
  5. custominsolubles removed by filtration
  6. concentrationthe filtrate concentrated
  7. custom(solvent removed)
  8. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-5fde71c3705f4d8f94d4e51f2a84bf80
Source dataset
uspto-grants-1979_08
Patent number
US04164407

Reaction notes

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