Methyl bromoacetate → HCID 22565520, compound

HRID 25077Notes

Reaction equation

HRID 25077 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:28])[NH:26][NH2:27].Br[CH2:30][C:31](OC)=[O:32]>CN(C)C=O>[O:32]=[C:31]1[CH2:30][S:28][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][NH:27]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 12137411(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothiohydrazide

Product 1

HCID 22565520HCID 22565520, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.00 g (2.50 mmol) of the starting material XVIII, 20 ml of dimethylformamide and 0.94 g (6.14 mmol) of methyl bromoacetate was stirred at 70° C. for 1.5 h. After dilution with water the precipitated crystals were filtered off and purified by refluxing in ethyl acetate to yield 0.41 g (37%) of the title compound; Mp.: 294-295° C. (dec.).

Workup

  1. filtrationAfter dilution with water the precipitated crystals were filtered off
  2. custompurified
  3. temperatureby refluxing in ethyl acetate

Sources & evidence

ORD record
ord-ef5d2a6d94954bcbb77a4dc951caacb0
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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