Water → HCID 86760093, compound

HRID 1826697Notes

Reaction equation

HRID 1826697 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[C:17]3[CH:18]=[C:19]4[O:24][CH2:23][O:22][C:20]4=[CH:21][C:16]=3[CH2:15][C:14]([C:25]([NH2:27])=[O:26])=[N:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl-].[Ca+2].[Cl-].O>C(O)C.ClCCl.C(#N)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[C:17]3[CH:18]=[C:19]4[O:24][CH2:23][O:22][C:20]4=[CH:21][C:16]=3[CH2:15][CH:14]([C:25]([NH2:27])=[O:26])[NH:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 86760092HCID 86760092, compound

Product 1

HCID 86760093HCID 86760093, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1.76 g (5.0 millimoles) of 5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-8-carboxylic acid-amide are suspended in a mixture of 75 ml ethanol and 75 ml of dichloro methane, whereupon 0.19 g (5.0 millimoles) of sodium-[tetrahydrido-borate(IV)] are added in one portion and a solution of 0.55 g (5.0 millimoles) of calcium chloride in 25 ml of ethanol is added dropwise. The reaction mixture is stirred at room temperature for 25 hours and evaporated in vacuo. The residue is heated to boiling in 100 ml of water for half an hour and filtered hot. The crude product obtained is heated to boiling in 50 ml of acetonitrile for half an hour, cooled with icecold water, filtered and washed with 20 ml of diethyl ether. Thus 1.27 g of the desired compound are obtained, yield 69%, mp.: 246–249° C.

Workup

  1. additionare added in one portion
  2. customevaporated in vacuo
  3. temperatureThe residue is heated
  4. waitto boiling in 100 ml of water for half an hour
  5. filtrationfiltered hot
  6. customThe crude product obtained
  7. temperatureis heated
  8. filtrationfiltered
  9. washwashed with 20 ml of diethyl ether

Sources & evidence

ORD record
ord-0a676cfcaf6945fe82e792c59063bb26
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

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