Hydrochloric Acid → HCID 13961192, compound

HRID 1197118Notes

Reaction equation

HRID 1197118 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[Mg].[CH3:10][C:11]1[O:16][C:15](=[O:17])[C:14]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:13]=2[N:12]=1.Cl>CCOCC>[C:11]([NH:12][C:13]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:14]=1[C:15]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8])=[O:17])(=[O:16])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 127541-Bromo-2-chlorobenzeneHCID 27965282,6-dimethyl-4H-3,1-benzoxazin-4-oneHCID 5462224Magnesium

Product 1

HCID 13961192HCID 13961192, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent prepared from 312.5 g (1.63 mol) of 2-bromochlorobenzene and 39.6 g (1.63 mol) of magnesium in 1.2 liters of anhydrous ether is added dropwise, in 2.5 hours, to a stirred solution of 270 g (1.54 mol) of 2,6-dimethyl-4H-3,1-benzoxazin-4-one in 4 liters of absolute ether at room temperature. The mixture is then allowed to react for a further 2 hours at the same temperature. While cooling in ice, the mixture is cautiously hydrolysed with 2N hydrochloric acid and then the aqueous phase is separated off. The organic phase is washed first with dilute sodium hydroxide solution and then with water. The organic phase is dried and concentrated. The resulting residue is induced to crystallise with isopropyl ether.

Workup

  1. customto react for a further 2 hours at the same temperature
  2. temperatureWhile cooling in ice
  3. customthe aqueous phase is separated off
  4. washThe organic phase is washed first with dilute sodium hydroxide solution
  5. customThe organic phase is dried
  6. concentrationconcentrated
  7. customto crystallise with isopropyl ether

Sources & evidence

ORD record
ord-6121a034348343e7a6c3f8091d41769d
Source dataset
uspto-grants-1992_05
Patent number
US05116971

Reaction notes

Loading…