Ammonia → HCID 15079735, compound

HRID 566293Notes

Reaction equation

HRID 566293 reaction equation
[Cl: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]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=S)[CH2:10][N:9]=1.[NH3:23].CO>O1CCCC1>[NH2:23][C:11]1[CH2:10][N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 12371433HCID 12371433, compound

Product 1

HCID 15079735HCID 15079735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 14 g of 5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepine-2(1H)-thione (J. B. Hester, A. D. Rudzik & B. V. Kamdar, J. Med. Chem., 1971, 14, 1078-1081) in 700 ml of tetrahydrofuran were added firstly 260 ml of 25% aqueous ammonia solution and then 50 ml of methanol. The solution was stirred at room temperature for 20 h. and then concentrated to about 25 ml in a vacuum. The crystalline precipitate was filtered off and recrystallized from dioxan. There were obtained 13.2 g of 2-amino-5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepine of m.p. 222-224° C.

Workup

  1. concentrationconcentrated to about 25 ml in a vacuum
  2. filtrationThe crystalline precipitate was filtered off
  3. customrecrystallized from dioxan

Sources & evidence

ORD record
ord-f0186301a3ac4ab9a4ed6c9998beb3d1
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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