Sodium Bicarbonate → HCID 21265984, compound

HRID 566296Notes

Reaction equation

HRID 566296 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH2:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]3[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:7]=3[N:6]2[CH:25]=1.C(=O)([O-])[OH:27].[Na+]>O1CCOCC1.O>[N+:22]([C:19]1[CH:20]=[CH:21][C:7]2[N:6]3[CH:25]=[C:3]([CH2:2][OH:27])[N:4]=[C:5]3[CH2:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:8]=2[CH:18]=1)([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 21265980HCID 21265980, compound

Product 1

HCID 21265984HCID 21265984, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5.1 g of 2-chloromethyl-8-nitro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepine in 70 ml of dioxan was treated with a solution of 1.54 g of sodium hydrogen carbonate in 30 ml of water and the mixture was stirred at 80° C. for 2.5 h. The mixture was filtered and the filtrate was made weakly acidic (pH 6 to 7) with aqueous 3N hydrochloric acid. The filtrate was evaporated in a vacuum and the residue was taken up in chloroform and water. The chloroform phase was washed with water, dried over sodium sulphate and evaporated in a vacuum. The crystalline residue (3.2 g) was dissolved in chloroform and chromatographed over 130 g of silica gel. With chloroform and with chloroform/ethanol 98:2 there were eluted small amounts of various impurities, with chloroform/ethanol 97:3 and 96:4 there was eluted 8-nitro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol. After recrystallization from ethanol there were obtained 2.45 g of pure 8-nitro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol of m.p. 250-251° C. which was converted into the hydrochloride (m.p. 295-297° C.).

Workup

  1. filtrationThe mixture was filtered
  2. customThe filtrate was evaporated in a vacuum
  3. washThe chloroform phase was washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated in a vacuum
  6. dissolutionThe crystalline residue (3.2 g) was dissolved in chloroform
  7. customchromatographed over 130 g of silica gel
  8. washWith chloroform and with chloroform/ethanol 98:2 there were eluted small amounts of various impurities
  9. washwith chloroform/ethanol 97:3 and 96:4 there was eluted 8-nitro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol
  10. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-22f1e71549d64f1aae0db1ab7844c12a
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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