Toluene → 4,5-dihydro-3,1-benzoxazepin-2(1H)-one

HRID 1041715Notes

Reaction equation

HRID 1041715 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[C:11](Cl)(Cl)=[O:12].C1(C)C=CC=CC=1>C1COCC1>[CH:7]1[C:3]2[CH2:4][CH2:5][O:6][C:11](=[O:12])[NH:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 79282o-Aminophenethyl alcohol

Product 1

HCID 111478994,5-dihydro-3,1-benzoxazepin-2(1H)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminophenethyl alcohol (4.0 g, 29.16 mmol) in THF (200 mL) was added a solution of 2M phosgene in toluene (17 mL, 34 mmol) at room temperature. The reaction was stirred for 15 minutes, concentrated, and purified with flash chromatography using ethyl acetate (5% 20%) in hexanes to yield 8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one (4 g, 84%): 1H NMR (300 MHz, CDCl3) δ 8.02 (bs, 1H), 7.17 (dt, 1H), 7.09 (d, 1H), 6.99 (dt, 1H), 6.90 (d, 1H), 4.51 (t, 2H), 3.21 (t, 2H).

Workup

  1. concentrationconcentrated
  2. custompurified with flash chromatography

Sources & evidence

ORD record
ord-2c4a34fd9f3e4fec8649e3af579e61a6
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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