Hydrochloric Acid → HCID 20406152, compound

HRID 2164304Notes

Reaction equation

HRID 2164304 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[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>C(OCC)C.C1C=CC=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]([C:14]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:13]=2[NH:12][C:11](=[O:16])[CH3:10])=[O:17])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99931-Bromo-4-fluorobenzeneHCID 27965282,6-dimethyl-4H-3,1-benzoxazin-4-oneHCID 5462224Magnesium

Product 1

HCID 20406152HCID 20406152, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard reagent prepared from 87.5 g (0.5 mole) of p-bromofluorobenzene and excess magnesium in 800 ml of diethyl ether was slowly added to a solution of 2,6-dimethyl-3,1-benzoxazine-4-one in 300 ml of dry benzene and 200 ml of dry diethyl ether at 0° C. The mixture was allowed to warm to room temperature and stirring was continued for 2 hr. The reaction mixture was cooled to -15° C. and 500 ml of 3N hydrochloric acid was added. After about 10 min additional stirring, the organic layer was separated and washed with dilute sodium hydroxide solution. The organic layer was concentrated and the residue was dissolved in a mixture of 600 ml of 95% ethanol and 300 ml of 6N hydrochloric acid. The precipitate (crude titled product) in the amount of 123 g (ca 91%) was recrystallized from cyclohexane to give tan crystals, m.p. 140°-145° C.

Workup

  1. temperatureThe reaction mixture was cooled to -15° C.
  2. waitAfter about 10 min additional stirring
  3. customthe organic layer was separated
  4. washwashed with dilute sodium hydroxide solution
  5. concentrationThe organic layer was concentrated
  6. dissolutionthe residue was dissolved in a mixture of 600 ml of 95% ethanol and 300 ml of 6N hydrochloric acid
  7. customThe precipitate (crude titled product) in the amount of 123 g (ca 91%) was recrystallized from cyclohexane
  8. customto give tan crystals, m.p. 140°-145° C.

Sources & evidence

ORD record
ord-4282fddac26845a3aec9b860de65f6b3
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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