Ammonia → HCID 21265982, compound

HRID 566295Notes

Reaction equation

HRID 566295 reaction equation
[NH3:1].[N+:2]([C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13](=S)[CH2:12][N:11]=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:22]=1)([O-:4])=[O:3]>O1CCCC1>[NH2:1][C:13]1[CH2:12][N:11]=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[CH:22]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=[CH:7][C:8]=2[N:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53784912,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepine-2-thione

Product 1

HCID 21265982HCID 21265982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 ml of 25% aqueous ammonia solution were added to a solution of 16 g of 7-nitro-5-phenyl-3H-1,4-benzodiazepine-2(1H)-thione (J. B. Hester, A. D. Rudzik & B. V. Kamdar, J.Med.Chem., 1971, 14, 1078-1081) in 850 ml of tetrahydrofuran. The solution was stirred at room temperature for 20 h. and then concentrated to about 50 ml in a vacuum. The crystalline precipitate was filtered off and recrystallized from dioxan. There were obtained 8.0 g of 2-amino-7-nitro-5-phenyl-3H-1,4-benzodiazepine which was used in this form for the next step.

Workup

  1. concentrationconcentrated to about 50 ml in a vacuum
  2. filtrationThe crystalline precipitate was filtered off
  3. customrecrystallized from dioxan

Sources & evidence

ORD record
ord-dcb968b02eac47f49498a5d1fcb6a06e
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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