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

HRID 25080Notes

Reaction equation

HRID 25080 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]([N:8]1[CH:14]([CH3:15])[CH2:13][C:12]2[CH:16]=[C:17]3[O:22][CH2:21][O:20][C:18]3=[CH:19][C:11]=2[C:10]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[N:9]1)=[S:7])=[O:4].BrBr.CO>C(Cl)(Cl)Cl>[CH3:15][CH:14]1[CH2:13][C:12]2[CH:16]=[C:17]3[O:22][CH2:21][O:20][C:18]3=[CH:19][C:11]=2[C:10]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[N:9][N:8]1[C:6]1[S:7][N:2]([CH3:1])[C:3](=[O:4])[N:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 86593814(+/-)-1-Methyl-3-{8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothioyl}-urea

Product 1

HCID 22565496(+/-)-8-Methyl-7-(2-methyl-3-oxo-2,3-dihydro-1,2,4-thiadiazol-5-yl)-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To an ice cooled stirred solution of 0.44 g (1.0 mmol) of the starting material XXVII in 8 ml of chloroform a solution of 0.19 g (1.2 mmol) of bromine in 3 ml of chloroform was added. After 0.5 h the reaction mixture was diluted with 15 ml of chloroform and washed with sodium hydrogen carbonate solution and water. The residue obtained on concentration was stirred with methanol and filtered to yield 0.36 g (82%) of the title compound. Mp.: 296° C. after recrystallization from ethyl acetate.

Workup

  1. additionwas added
  2. washwashed with sodium hydrogen carbonate solution and water
  3. customThe residue obtained on concentration
  4. filtrationfiltered

Sources & evidence

ORD record
ord-20f6119f8dc742118769727308234a2c
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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