Dimethylformamide → (+/-)-8-Methyl-7-(4-methyl-thiazol-2-yl)-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25064

Reaction equation

HRID 25064 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25](=[S:27])[NH2:26].Cl[CH2:29][C:30](=O)[CH3:31].CN(C)C=O>O>[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[N:4][N:3]1[C:25]1[S:27][CH:29]=[C:30]([CH3:31])[N:26]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 12137394(+/-)-8-Methyl-5-(4-nitrophenyl)-7-thiocarbamoyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Product 1

HCID 12137423(+/-)-8-Methyl-7-(4-methyl-thiazol-2-yl)-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 0.76 g (1.98 mmol) of the starting material I, 1.10 g (11.88 mmol) of chloroacetone and 15 ml of dimethylformamide was stirred at 80-90° C. for 40 min. Then the reaction mixture was diluted with water, the precipitated crystals were filtered off, dried and purified by refluxing in ethanol to yield 0.69 g (82%) of the title compound; Mp.: 188-189° C.

Workup

  1. filtrationthe precipitated crystals were filtered off
  2. customdried
  3. custompurified
  4. temperatureby refluxing in ethanol

Sources & evidence

ORD record
ord-9acdb13ea24346d98b1bb6f6e7dc3742
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Linked notes

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