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

HRID 1642056Notes

Reaction equation

HRID 1642056 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])=[O:4].CO.[NH3:24]>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:24]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:7]=2[CH:8]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 887MethanolHCID 534406762-Bromo-N-[4-bromo-2-(2-fluorobenzoyl)phenyl]acetamide

Product 1

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

Procedure

The product from Step 1 (21.17 g, 51 mmol) was dissolved in ammonia, 2M in methanol (400 mL, 800 mmol) that was further saturated with anhydrous ammonia. The solution was heated to reflux for 16 hr overnight, and allowed to cool to room temperature. The solution was concentrated and the residue was dissolved in ethyl acetate and water. The ethyl acetate layer was washed twice with water, dried with brine, and concentrated to give a yellow solid. The solid was recrystallized from ethyl acetate/hexane to give a white powder that was washed with hexane and air dried (9.65 g, 56.8%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 16 hr overnight
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate layer was washed twice with water
  6. dry with materialdried with brine
  7. concentrationconcentrated
  8. customto give a yellow solid
  9. customThe solid was recrystallized from ethyl acetate/hexane
  10. customto give a white powder that
  11. washwas washed with hexane and air
  12. customdried (9.65 g, 56.8%)

Sources & evidence

ORD record
ord-722fe6c28f8f4c6c9243a1465bcd3051
Source dataset
uspto-grants-2012_02
Patent number
US08119629B2

Reaction notes

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