Ethylene Glycol → 2-hydroxyethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

HRID 1902403Notes

Reaction equation

HRID 1902403 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1.[C-]#N.[K+].C(O)C[OH:28]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH2:19][OH:28])=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 3373FlumazenilHCID 9032Potassium Cyanide

Product 1

HCID 205153142-hydroxyethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

Conditions

Temperature
130 °C

Procedure

A mixture of 6.08 g (20 mmol) of ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 100 mg of potassium cyanide and 60 ml of ethyleneglycol is stirred at 130° C. for 6 hours and subsequently evaporated. After taking up the residue in chloroform, the solution is washed with water, dried over magnesium sulphate and evaporated. After recrystallization of the crude product from ethyl acetate, there is obtained 2-hydroxyethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 202°-204° C.

Workup

  1. customsubsequently evaporated
  2. washthe solution is washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customAfter recrystallization of the crude product from ethyl acetate

Sources & evidence

ORD record
ord-b466f5d406a74acfa1a84b41986b1477
Source dataset
uspto-grants-1982_12
Patent number
US04363762

Reaction notes

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