Dimethylformamide → HCID 14357896, compound

HRID 1414361Notes

Reaction equation

HRID 1414361 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH2:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:7]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:6]=3[N:5]2[CH:23]=1.[Cl-].CC(=[NH2+])C.[CH3:29][N:30]([CH3:33])[CH:31]=O>>[CH3:29][N:30]([CH2:33][C:23]1[N:5]2[C:6]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:7]=3[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:9][CH2:10][C:4]2=[N:3][C:2]=1[CH3:1])[CH3:31]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 127071318-chloro-6-(o-chlorophenyl)-2-methyl-4H-imidazo[1,2-a][1,4]benzodiazepineHCID 21939857Dimethylmethyleneammonium chloride

Product 1

HCID 14357896HCID 14357896, compound

Procedure

In the manner given in Example 1, 6.844 (20 mmol) of 2-methyl-8-chloro-6-(o-chlorophenyl)-4H-imidazo[1,2-a]-[1,4]benzodiazepine is treated with 40.0 mmol of dimethylmethylene ammonium chloride in dimethylformamide during 2 hours at 100° C. The reaction mixture is quenched on ice, neutralized with 10% aqueous sodium hydroxide and chromatographed over silica gel with 1 l. fractions of 3% methanol/97% chloroform solutions to give 1-(dimethylamino)methyl-2-methyl-8-chloro-6-(o-chlorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepine of melting point 191°-194° C.

Workup

  1. customThe reaction mixture is quenched on ice
  2. customchromatographed over silica gel with 1 l

Sources & evidence

ORD record
ord-254c7f22233f447aa8238aaf92a5b1d2
Source dataset
uspto-grants-1977_01
Patent number
US04001261

Reaction notes

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