Ethyl Acetate → 7-Bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

HRID 1816873Notes

Reaction equation

HRID 1816873 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10]Cl)=[C:4]([C:13]([OH:20])([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[CH3:14])[CH:3]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9](=[O:12])[CH2:10][O:20][C:13]([CH3:14])([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 68864161N-[4-Bromo-2-(1-hydroxy-1-thien-2-ylethyl)phenyl]-2-chloroacetamide

Product 1

HCID 688661097-Bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-bromo-2-(1-hydroxy-1-thien-2-ylethyl)phenyl]-2-chloroacetamide (1.29 g, 3.44 mmol) in anhydrous THF (20 mL) was added at 0 under nitrogen sodium hydride (60% in mineral oil, 0.38 g, 9.5 mmol). After addition, the reaction mixture was stirred for 3 h, treated with an aqueous saturated ammonium chloride solution (30 mL). Ethyl acetate (50 mL) was added and organic layer separated, dried (Mg2SO4), and concentrated to yield the title compound as a white solid (1.1 g, 96%). 1H-NMR (DMSO-d6) δ 10.13 (s, 1H), 7.57 (dd, J=5.0, 1.0 Hz, 1H), 7.47 (dd, J=8.6, 1.4 Hz, 1H), 7.39 (d, J=1.67 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H), 7.00 (m, 1H), 6.88 (dd, J=2.6, 0.9 Hz, 1H), 4.18 (d, J=15.8 Hz, 1H), 4.03 (d, J=16.3 Hz, 1H), 1.99 (s, 3H). MS (ES) m/z 338/340 ([M+H]+, 100%).

Workup

  1. additionAfter addition
  2. customorganic layer separated
  3. dry with materialdried (Mg2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1a4525a9971f4e838d9f02c9c7e0657f
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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