1,1'-Carbonyldiimidazole → 6-Bromo-3,4-dihydro-2H-1,3-benzoxazin-2-one

HRID 1923485Notes

Reaction equation

HRID 1923485 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[OH:10].[C:11](N1C=CN=C1)(N1C=CN=C1)=[O:12]>C1COCC1>[Br:9][C:7]1[CH:6]=[CH:5][C:4]2[O:10][C:11](=[O:12])[NH:1][CH2:2][C:3]=2[CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 2240102-(Aminomethyl)-4-bromophenol

Product 1

HCID 454804666-Bromo-3,4-dihydro-2H-1,3-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(aminomethyl)-4-bromophenol (I) (1.16 g, 5.7 mmol), triethylamthylamine (III) and carbonyldiimidazole (II) (1.86 g, 11.5 mmol) in anhydrous THF (100 ml) is refluxed for 4 hours. The solvent is evaporated and the residue dissolved in dichloromethane (DCM) (100 ml). The organic solution is washed with 1N HCl (20 ml×3) and then with brine (50 ml). The solvent is then evaporated and the resulting residue is purified by chromatography to give 6-bromo-3,4-dihydrobenzo[e][1,3]oxazin-2-one as a white powder.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in dichloromethane (DCM) (100 ml)
  3. washThe organic solution is washed with 1N HCl (20 ml×3)
  4. customThe solvent is then evaporated
  5. customthe resulting residue is purified by chromatography

Sources & evidence

ORD record
ord-d68a4d85a0964a6d87997aaa843c9472
Source dataset
uspto-grants-2012_05
Patent number
US08178526B2

Reaction notes

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