Menthyl chloroformate → 1methyl-4-menthyloxycarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one

HRID 442323Notes

Reaction equation

HRID 442323 reaction equation
[O-2].[Mg+2].[CH:3]1([CH3:16])[CH2:8][CH2:7][CH:6]([CH:9]([CH3:11])[CH3:10])[CH:5]([O:12][C:13](Cl)=[O:14])[CH2:4]1.[CH3:17][N:18]1[C:24]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:23]=2[CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:21][CH2:20][C:19]1=[O:36]>CC(C)=O>[CH3:17][N:18]1[C:24]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:23]=2[CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:21]([C:13]([O:12][CH:5]2[CH:6]([CH:9]([CH3:11])[CH3:10])[CH2:7][CH2:8][CH:3]([CH3:16])[CH2:4]2)=[O:14])[CH2:20][C:19]1=[O:36]

Participants

5

Reactant 3

HCID 151928Menthyl chloroformateHCID 30819844,5-DihydrodiazepamHCID 6850729Magnesium monoxide

Product 1

HCID 681251631methyl-4-menthyloxycarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.2 g. of magnesium oxide and 1.21 g. (0.0055 moles) of menthyloxycarbonyl chloride are added to a solution of 1.34 g. (0.005 moles) of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 20 ml. of acetone, and the mixture is stirred overnight. Next day carbon is added to the mixture, the suspension is filtered, and the filtrate is evaporated to dryness. The oily residue is dissolved in 20 ml. of ethyl acetate, the solution is shaken with 3×5 ml. of 0.1 N hydrochloric acid, the organic phase is washed with water until neutral, then dried over sodium sulfate. The drying agent is filtered off, and the filtrate is evaporated. The residue is admixed with hexane, and the solids are filtered off. 0.82 g. of 1methyl-4-menthyloxycarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one, melting at 144°- 144.5° C., are obtained. The obtained substance is recrystallized from a mixture of ethanol and water. Rf2 = 0.8.

Workup

  1. additionNext day carbon is added to the mixture
  2. filtrationthe suspension is filtered
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe oily residue is dissolved in 20 ml
  5. washof 0.1 N hydrochloric acid, the organic phase is washed with water until neutral,
  6. dry with materialthen dried over sodium sulfate
  7. filtrationThe drying agent is filtered off
  8. customthe filtrate is evaporated
  9. filtrationthe solids are filtered off

Sources & evidence

ORD record
ord-8b4e3b0c2dd449fc9ac6ee7e2f96066b
Source dataset
uspto-grants-1977_08
Patent number
US04045433

Reaction notes

Loading…