Sodium Bicarbonate → HCID 21265969, compound

HRID 566310Notes

Reaction equation

HRID 566310 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][N:13]=3)[C:8]3[CH:18]=[C:19]([I:22])[CH:20]=[CH:21][C:7]=3[N:6]2[CH:23]=1.C(=O)([O-])[OH:25].[Na+]>O1CCOCC1.O>[I:22][C:19]1[CH:20]=[CH:21][C:7]2[N:6]3[CH:23]=[C:3]([CH2:2][OH:25])[N:4]=[C:5]3[CH2:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:8]=2[CH:18]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 21266016HCID 21266016, compound

Product 1

HCID 21265969HCID 21265969, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.15 g of 2-chloromethyl-8-iodo-6-(2-pyridyl)-4H-imidazo[1,2-a][1,4]benzodiazepine in 40 ml of dioxan was treated with a solution of 0.28 g of sodium hydrogen carbonate in 10 ml of water and stirred at 80° C. for 1.5 h. The mixture was evaporated in a vacuum. The residue was partitioned between chloroform and aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted three times with chloroform. The chloroform extracts were dried over sodium sulphate, concentrated to 30 ml in a vacuum and chromatographed over 50 g of silica gel. 1.05 g of the desired product were eluted with chloroform/ethanol mixtures containing 3 to 7% ethanol. After recrystallization from ethyl acetate/diethyl ether there was obtained 0.955 g of 8-iodo-6-(2-pyridyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol of m.p. 206-207° C. which was converted into the hydrochloride (dec. above 300° C.).

Workup

  1. customThe mixture was evaporated in a vacuum
  2. customThe residue was partitioned between chloroform and aqueous sodium hydrogen carbonate solution
  3. extractionThe aqueous phase was extracted three times with chloroform
  4. dry with materialThe chloroform extracts were dried over sodium sulphate
  5. concentrationconcentrated to 30 ml in a vacuum
  6. customchromatographed over 50 g of silica gel
  7. wash1.05 g of the desired product were eluted with chloroform/ethanol mixtures
  8. additioncontaining 3 to 7% ethanol
  9. customAfter recrystallization from ethyl acetate/diethyl ether there

Sources & evidence

ORD record
ord-65718ba8521a47cc9a21ca57def6d01a
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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