Cyclohexanol → HCID 20434837, compound

HRID 1154472Notes

Reaction equation

HRID 1154472 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=3[C:13](=[O:21])[N:12]([CH3:22])[CH2:11][C:10]=12)=[O:5])[CH3:2].[CH:23]1(O)[CH2:28]CC[CH2:25][CH2:24]1>CCO.CCO.CCO.CCO.[Ti]>[Cl:20][C:19]1[C:14]2[C:13](=[O:21])[N:12]([CH3:22])[CH2:11][C:10]3[N:9]([CH:8]=[N:7][C:6]=3[C:4]([O:3][CH:1]3[CH2:25][CH2:24][CH2:23][CH2:28][CH2:2]3)=[O:5])[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 71231Sarmazenil

Product 1

HCID 20434837HCID 20434837, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 8.72 g (27 mmol) of ethyl-7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 2 g (9 mmol) of tetraethyl orthotitanate and 27 g (270 mmol) of cyclohexanol is stirred at 125° overnight, evaporated to dryness, the residue is taken up in chloroform, the chloroform solution is washed successively with 40 ml of 5N hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. By recrystallization from ethanol and ether there is obtained cyclohexyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 208°-209°.

Workup

  1. customevaporated to dryness
  2. washthe chloroform solution is washed successively with 40 ml of 5N hydrochloric acid and saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customBy recrystallization from ethanol and ether

Sources & evidence

ORD record
ord-b63f704a164846e0bbcabeafdf681510
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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