Methanol → HCID 20317275, compound

HRID 867059Notes

Reaction equation

HRID 867059 reaction equation
[N:1]([CH2:4][C:5](=[N:9][C:10]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)[O:6][CH2:7][CH3:8])=[N+]=[N-].CO.[Cl-].[NH4+]>[Zn].O>[Cl:24][C:21]1[CH:22]=[CH:23][C:10]2[N:9]=[C:5]([O:6][CH2:7][CH3:8])[CH2:4][N:1]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]=2[CH:20]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 20317279HCID 20317279, compound

Product 1

HCID 20317275HCID 20317275, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a solution of 1.7 part of 2-(2-azido-1-ethoxyethylideneamino)-5-chlorobenzophenone produced in Step (2) of Example 1 in 50 parts by volume of methanol is added a solution of 1.6 part of ammonium chloride in 5 parts by volume of water. To the mixture is added 1 part of zinc powder with stirring. After 10 minutes, the resulting precipitates are removed by filtration. The filtrate is poured into 100 parts by volume of water, and extracted with ethyl acetate. Ethyl acetate layer is washed with water and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure to give 7-chloro-2-ethoxy-5-phenyl-3H-1,4-benzodiazepine as an oily substance.

Workup

  1. customthe resulting precipitates
  2. customare removed by filtration
  3. additionThe filtrate is poured into 100 parts by volume of water
  4. extractionextracted with ethyl acetate
  5. washEthyl acetate layer is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-53bae30e78f442138e39cf1585c1776d
Source dataset
uspto-grants-1978_07
Patent number
US04102881

Reaction notes

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