Ammonia → HCID 21265972, compound

HRID 566278Notes

Reaction equation

HRID 566278 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=S)[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:7]=2[CH:21]=1>O1CCCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]=[C:11]([NH2:1])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:7]=2[CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3081966N-Desmethylquazepam

Product 1

HCID 21265972HCID 21265972, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

800 ml of aqueous ammonia solution (25%) were added to a solution of 27.6 g of 7-chloro-5-(2-fluorophenyl)-3H-1,4-benzodiazepine-2(1H)-thione (J. B. Hester jr., A. D. Rudzik and B. V. Bharat, J.Med. Chem., 1971, 14, 1078-1081) in 900 ml of tetrahydrofuran and the mixture was stirred intensively at room temperature for 72 h. The separated organic phase was concentrated in a vacuum to about 50 ml and the crystals which thereby separated were filtered off. Drying was carried out in a vacuum at 50° C., firstly over calcium chloride, then over phosphorus pentoxide. There were obtained 22.8 g (87%) of 7-chloro-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2-ylamine as a pale yellow crystalline powder of m.p. 248-249° C. (dec.) which was used without further purification for the steps described below.

Workup

  1. concentrationThe separated organic phase was concentrated in a vacuum to about 50 ml
  2. customthe crystals which thereby separated
  3. filtrationwere filtered off
  4. customDrying
  5. customwas carried out in a vacuum at 50° C., firstly over calcium chloride

Sources & evidence

ORD record
ord-9c6f0006000c435cbdbe4c9608f0f54e
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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