1,1'-Carbonyldiimidazole → HCID 11197457, compound

HRID 661843Notes

Reaction equation

HRID 661843 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH2:21][NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[O:20][C:1](=[O:2])[N:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:21][C:16]=2[CH:15]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 534400192-(Anilinomethyl)-4-bromophenol

Product 1

HCID 11197457HCID 11197457, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Step 2 Carbonyldiimidazole (0.874 g, 5.39 mmol) and DMAP (0.088 g, 0.719 mmol) were added to a solution of 4-bromo-2-((phenylamino)methyl)phenol (1.00 g, 3.60 mmol) in DCM (100 mL) and the resulting mixture was stirred at rt for 60 h. The mixture was diluted with hexanes (100 mL), washed with NaHCO3 (aq) (2×25 mL), 1 M hydrochloric acid (25 mL) and brine (25 mL), dried and filtered through a pad of silica gel. The solids were rinsed with 1:1 EtOAc-hexane and the filtrate was concentrated to give 6-bromo-3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-2-one as a white solid (1.09 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ 7.41-7.56 (3H, m), 7.30-7.41 (3H, m), 7.21-7.29 (1H, m), 7.01 (1H, d, J=8.80 Hz), 4.80 (2H, s). Mass spectrum m/z 304, 306 (M+H)+.

Workup

  1. washwashed with NaHCO3 (aq) (2×25 mL), 1 M hydrochloric acid (25 mL) and brine (25 mL)
  2. customdried
  3. filtrationfiltered through a pad of silica gel
  4. washThe solids were rinsed with 1:1 EtOAc-hexane
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cd11ba51779b46e68f8fa9755a0a4182
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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