1,1'-Carbonyldiimidazole → 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 2209289Notes

Reaction equation

HRID 2209289 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]([CH3:10])([CH3:11])[O:12][C:18](=[O:19])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 571557062-(2-Amino-4-bromophenyl)propan-2-ol

Product 1

HCID 468564867-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-oneYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Into the solution of 2-(2-amino-4-bromophenyl)propan-2-ol (2.3 g) in THF (50 mL) was added CDI (1.95 g) at rt., then the mixture was warmed to 60° C. and stirred for overnight. After solvent removal, the residue was dissolved in ethyl acetate and washed with 1M of HCl(aq) and brine, and dried with dry agent. After removal of the solvent, the residue was crystallized from DCM and hexane to provide 2.3 g of 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.37 was synthesized. LCMS [M+H]+: 252.71. 1H NMR (400 MHz, Chloroform-d) δ 9.30 (s, 1H), 7.18 (d, d, J=8.2, 1.8 Hz, 1H), 7.06 (d, J=1.8 Hz, 1H), 6.99 (d, J=8.2 Hz, 1H), 1.71 (s, 6H).

Workup

  1. customAfter solvent removal
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1M of HCl(aq) and brine
  4. customdried
  5. customwith dry agent
  6. customAfter removal of the solvent
  7. customthe residue was crystallized from DCM and hexane

Sources & evidence

ORD record
ord-1b5f412ef6184224aafa7c9ad43213fe
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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