Ammonia → 2-amino-7-chloro-5-(2-pyridyl)-3H-1,4-benzodiazepine

HRID 566303Notes

Reaction equation

HRID 566303 reaction equation
[NH3:1].CO.[Cl:4][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][N:17]=3)[C:9]=2[CH:22]=1>O1CCCC1>[NH2:1][C:13]1[CH2:12][N:11]=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:9]2[CH:22]=[C:5]([Cl:4])[CH:6]=[CH:7][C:8]=2[N:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 212659987-chloro-5-(2-pyridyl)-3H-1,4-benzodiazepine-2(1H)-thione

Product 1

HCID 212660152-amino-7-chloro-5-(2-pyridyl)-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 ml of 25% aqueous ammonia solution and 100 ml of methanol were added to a solution of 18.5 g of 7-chloro-5-(2-pyridyl)-3H-1,4-benzodiazepine-2(1H)-thione in 800 ml of tetrahydrofuran. The mixture was stirred at room temperature for 17 h., with the solution which formed being concentrated to about 200 ml in a vacuum. The crystals were filtered off, washed with water and dried, stirred in 25 ml of dioxan at 100° C., cooled and filtered off. There were obtained 16.3 g of 2-amino-7-chloro-5-(2-pyridyl)-3H-1,4-benzodiazepine which was used without further purification for the next step. A sample recrystallized from dioxan melted at 213-215° C.

Workup

  1. customformed
  2. concentrationbeing concentrated to about 200 ml in a vacuum
  3. filtrationThe crystals were filtered off
  4. washwashed with water
  5. customdried
  6. stirringstirred in 25 ml of dioxan at 100° C.
  7. temperaturecooled
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-b22cd19a61a44ce1b53c4b85d87bfb7e
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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