Lawesson's reagent → 3-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-6-thione

HRID 223216Notes

Reaction equation

HRID 223216 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=O)[N:8]([CH3:17])[CH2:7][C:6]=12.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:27]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[S:27])[N:8]([CH3:17])[CH2:7][C:6]=12

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 205232833-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 205232813-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-6-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.71 g (15 mmol) of 3-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 10 ml of toluene are heated to boiling under reflux for 4 hours together with 3.03 g (7.5 mmol) of 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide. The solution is washed with water and evaporated. By chromatography on a silica gel column and subsequent recrystallization from ethyl acetate there is obtained 3-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-6-thione of melting point 197.5°-198.5°.

Workup

  1. washThe solution is washed with water
  2. customevaporated
  3. customBy chromatography on a silica gel column and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ef9ca3a58a36403eadea88bd1bfdf39f
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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