Ethanol → 7-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1365056Notes

Reaction equation

HRID 1365056 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][NH2:11])=[C:4]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=O)[CH:3]=1.C(O)C>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9](=[O:12])[CH2:10][N:11]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 57732437N-[4-Bromo-2-(2-fluorobenzoyl)phenyl]glycinamide

Product 1

HCID 129470247-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneYield 78.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A round-bottomed flask was charged with N1-{4-bromo-2-[(2-fluorophenyl)carbonyl]-phenyl}glycinamide (135 mg), ethanol (3 mL) and acetic acid (0.5 mL). The mixture was heated to reflux for 15 min, then cooled and concentrated to dryness. The residue was treated with a saturated solution of sodium bicarbonate and stirred for 10 min. before extracting with ethyl acetate. The combined organics were dried over magnesium sulfate then filtered and concentrated to dryness. The residue was reconcentrated from diethyl ether to provide 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (100 mg) as a light yellow foam. H1 NMR (d6-dmso): 10.74 (br s, 1H), 7.71 (dd, 1H), 7.52-7.59 (m, 2H), 7.15-7.34 (m, 4H), 4.20 (s, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 min
  3. temperaturecooled
  4. concentrationconcentrated to dryness
  5. additionThe residue was treated with a saturated solution of sodium bicarbonate
  6. extractionbefore extracting with ethyl acetate
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationthen filtered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1d363e8249ba4b969086f0f016140dd3
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

Loading…