Hydrochloric Acid → HCID 21265959, compound

HRID 566292Notes

Reaction equation

HRID 566292 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][C:13]=3[F:18])[C:8]3[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:7]=3[N:6]2[CH:26]=1.C(=O)([O-])[O-:28].[Na+].[Na+].Cl>O1CCOCC1.O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[C:8]2[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:7]=2[N:6]2[CH:26]=[C:3]([CH2:2][OH:28])[N:4]=[C:5]2[CH2:11][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 21265987HCID 21265987, compound

Product 1

HCID 21265959HCID 21265959, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 12 g of 2-chloromethyl-6-(2-fluorophenyl)-8-nitro-4H-imidazo [1,2-a][1,4]benzodiazepine in 100 ml of dioxan was treated with a solution of 3.5 g of sodium carbonate in 50 ml of water and stirred at 80° C. for 2.5 h. Then, the mixture was made weakly acidic (pH 6 to 7) with aqueous 3N hydrochloric acid and evaporated in a vacuum. The residue was taken up in chloroform, washed twice with water, dried over sodium sulphate and evaporated in a vacuum. The residue was dissolved in chloroform and chromatographed over 250 g of silica gel. With chloroform/ethanol 98:2 there were isolated a small amount of impurities, with chloroform/,6thanol 98:2 there was eluted 6-(2-fluorophenyl)-8-nitro-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol. After recrystallization from chloroform there were obtained 5.8 g of 6-(2-fluorophenyl)-8-nitro-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol of m.p. 230-231° C. This was converted into the hydrochloride of m.p. 239-241° C.

Workup

  1. customevaporated in a vacuum
  2. washwashed twice with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated in a vacuum
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed over 250 g of silica gel
  7. customWith chloroform/ethanol 98:2 there were isolated a small amount of impurities
  8. washwith chloroform/,6thanol 98:2 there was eluted 6-(2-fluorophenyl)-8-nitro-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol
  9. customAfter recrystallization from chloroform

Sources & evidence

ORD record
ord-0851b67d3d124ecba33ab4b79471aafb
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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