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

HRID 25069

Reaction equation

HRID 25069 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].Br[CH:29]([CH3:35])[C:30](OCC)=[O:31].CN(C)C=O>O>[CH3:35][CH:29]1[S:27][C:25]([N:3]2[CH:2]([CH3:1])[CH2:8][C:7]3[CH:9]=[C:10]4[O:15][CH2:14][O:13][C:11]4=[CH:12][C:6]=3[C:5]([C:16]3[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[N:4]2)=[N:26][C:30]1=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 79040Ethyl 2-bromopropionateHCID 12137394(+/-)-8-Methyl-5-(4-nitrophenyl)-7-thiocarbamoyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Product 1

HCID 12137432(+/-)-7-(4,5-Dihydro-5-methyl-4-oxo-thiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1.00 g (2.60 mmol) of the starting material I, 0.94 g (5.19 mmol) of ethyl 2-bromopropionate and 10 ml of dimethylformamide was stirred at 80-90° C. for 2 h. After diluting with water the obtained crude product was purified by refluxing in 15 ml of ethanol to yield 1.08 g (95%) of the title compound; Mp.: 213-214° C.

Workup

  1. customobtained crude product
  2. customwas purified
  3. temperatureby refluxing in 15 ml of ethanol

Sources & evidence

ORD record
ord-7485b3d401664163aaf0601da93eec85
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Linked notes

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