HCID 178500500, compound → HCID 21482313, compound

HRID 1415602Notes

Reaction equation

HRID 1415602 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][N:15]=2)[C:10]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:9]=2[N:8]=1)[CH3:5]>C(COC)OC.[Ti](Cl)(Cl)(Cl)Cl>[Cl:24][C:21]1[CH:22]=[CH:23][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][N:15]=3)[C:10]=2[CH:20]=1

Participants

4

Reactant 1

HCID 178500500HCID 178500500, compound

Product 1

HCID 21482313HCID 21482313, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-[[7-chloro-5-(2-pyridyl)-3H-1,4-benzodiazepin-2-yl]amino]propionaldehyde dimethyl acetal in monoglyme is treated with titanium tetrachloride first at room temperature, then under reflux. The reaction mixure is cooled, neutralized, and extracted with chloroform. The chloroform layer is concentrated in vacuo and the resulting residue crystallized to give 8-chloro-2-methyl-6-(2-pyridyl)-4H-imidazo[1,2-a][1,4]benzodiazepine.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixure is cooled
  3. extractionextracted with chloroform
  4. concentrationThe chloroform layer is concentrated in vacuo
  5. customthe resulting residue crystallized

Sources & evidence

ORD record
ord-b057e76255634b1eb93d6e4a96860511
Source dataset
uspto-grants-1977_01
Patent number
US04005099

Reaction notes

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