Sodium Bicarbonate → HCID 21265996, compound

HRID 566298Notes

Reaction equation

HRID 566298 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]([I:23])[CH:21]=[CH:22][C:7]=3[N:6]2[CH:24]=1.C(=O)([O-])[OH:26].[Na+]>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]([I:23])[CH:21]=[CH:22][C:7]=2[N:6]2[CH:24]=[C:3]([CH2:2][OH:26])[N:4]=[C:5]2[CH2:11][N:10]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70236918HCID 70236918, compound

Product 1

HCID 21265996HCID 21265996, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.2 g of 2-chloromethyl-6-(2-fluorophenyl)-8-iodo-4H-imidazo [1,2-a][1,4]benzodiazepine in 20 ml of dioxan was treated with a solution of 0.4 g of sodium hydrogen carbonate in 10 ml of water and the mixture was stirred at 80° C. for 2 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 residue was recrystallized from ethanol. There was obtained 0.6 g of amorphous 6-(2-fluorophenyl)-8-iodo-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol which was converted into the crystalline hydrochloride (m.p. 274-276° 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. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-556ee24ddc0a40deb889a95d74655d09
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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