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Sodium Bicarbonate → HCID 21266017, compound

HRID 566305
Notes
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Reaction equation

HRID 566305 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]([Cl:22])[CH:20]=[CH:21][C:7]=3[N:6]2[CH:23]=1.C(=O)([O-])[OH:25].[Na+]>O1CCOCC1.O>[Cl: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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 21265968HCID 21265968, compound

Product 1

HCID 21266017HCID 21266017, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2.0 g of 2-chloromethyl-8-chloro-6-(2-pyridyl)-4H-imidazo [1,2-a][1,4]benzodiazepine in 50 ml of dioxan was treated with a solution of 0.62 g of sodium hydrogen carbonate in 18 ml of water and the mixture was stirred at 80° C. for 1.5 h. The mixture was evaporated in a vacuum. The residue was partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted twice with dichloromethane. The dichloromethane extracts were dried over magnesium sulphate and chromatographed over 100 g of silica gel. 1.7 g of the desired product were eluted with dichloromethane/ethanol mixtures containing 8 to 12% ethanol. After recrystallization from ethyl acetate/diethyl (sic) ether there were obtained 1.65 g of 8-chloro-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 dichloromethane and aqueous sodium hydrogen carbonate solution
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  4. dry with materialThe dichloromethane extracts were dried over magnesium sulphate
  5. customchromatographed over 100 g of silica gel
  6. wash1.7 g of the desired product were eluted with dichloromethane/ethanol mixtures
  7. additioncontaining 8 to 12% ethanol
  8. customAfter recrystallization from ethyl acetate/diethyl (sic) ether there

Sources & evidence

ORD record
ord-1b7c7c7c144f4c4daa4a8cec20798648
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06174881B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes