Ammonia → Imidazenil

HRID 1034412Notes

Reaction equation

HRID 1034412 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:20]=[N:21][C:22]([C:23]([OH:25])=O)=[C:11]2[CH2:10][N:9]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH3:32]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:20]=[N:21][C:22]([C:23]([NH2:32])=[O:25])=[C:11]2[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 24819Phosphorus pentachlorideHCID 15292435HCID 15292435, compound

Product 1

HCID 119194Imidazenil

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3 g (7.5 mmol) of 6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 300 mL of methylene chloride and 2.25 g (10.8 mmol) of phosphorus pentachloride was stirred at room temperature for 2 hours. Ammonia gas was then introduced until the mixture was basic. After layering with 20 mL of concentrated aqueous ammonia, the mixture was stirred for 15 minutes. The methylene chloride was washed with water, dried and evaporated. The residue was crystallized from ethanol/water to yield 2.4 g of product having the above formula. A second crop of 0.4 g was obtained from the mother liquor for a total yield of 2.8 g. For analysis, a sample of the product was recrystallized from methylene chloride/ethanol and had m.p. 298°-299° C.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. washThe methylene chloride was washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was crystallized from ethanol/water

Sources & evidence

ORD record
ord-630c8b1d732049e49983d7325030958f
Source dataset
uspto-grants-1994_05
Patent number
US05317018

Reaction notes

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