HCID 178500499, compound → 8-chloro-6-(o-chlorophenyl)-2-methyl-4H-imidazo[1,2-a][1,4]benzodiazepine

HRID 1415600Notes

Reaction equation

HRID 1415600 reaction equation
CO[CH:3](OC)[CH:4]([NH:6][C:7]1[CH2:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:10]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:9]=2[N:8]=1)[CH3:5]>[Ti](Cl)(Cl)(Cl)Cl.C(COC)OC>[Cl:25][C:22]1[CH:23]=[CH:24][C:9]2[N:8]3[CH:3]=[C:4]([CH3:5])[N:6]=[C:7]3[CH2:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:10]=2[CH:21]=1

Participants

4

Reactant 1

HCID 178500499HCID 178500499, compound

Product 1

HCID 127071318-chloro-6-(o-chlorophenyl)-2-methyl-4H-imidazo[1,2-a][1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A sample of 2-[[7-chloro-5-(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl]amino]propionaldehyde dimethyl acetal (2.03 g., 5.00 mmol), dissolved in 60 ml. of monoglyme, is treated with 0.75 ml. (1.30 g., 6.85 mmol) of (reagent-grade) titanium tetrachloride. A vigorous reaction takes place and a brown solid precipitates in the reaction flask. The mixture is refluxed under nitrogen for 4 hours. The reaction mixture is cooled to room temperature, poured into 250 ml. of cold 5% aqueous sodium hydroxide and extracted with chloroform (400 ml.). The chloroform layer is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a solid. After crystallization 960 mg. of 8-chloro-2-methyl-6-(o-chlorophenyl)-4H-imidazo[1,2-a][1,4]-benzodiazepine of melting point 169.5° -170.5° C. is obtained.

Workup

  1. customA vigorous reaction
  2. customa brown solid precipitates in the reaction flask
  3. temperatureThe mixture is refluxed under nitrogen for 4 hours
  4. additionpoured into 250 ml
  5. extractionof cold 5% aqueous sodium hydroxide and extracted with chloroform (400 ml.)
  6. washThe chloroform layer is washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo to a solid
  9. customAfter crystallization 960 mg

Sources & evidence

ORD record
ord-ac9c1104d3ab49b2a99b1e96adea2cc1
Source dataset
uspto-grants-1977_01
Patent number
US04005099

Reaction notes

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