Phosgene → 4-chlorocarbonyl-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 2351376Notes

Reaction equation

HRID 2351376 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6]=12.[C:17](Cl)([Cl:19])=[O:18]>ClCCl.C1(C)C=CC=CC=1>[Cl:19][C:17]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[NH:10][C:11](=[O:12])[C:5]2=[CH:4][S:3][C:2]([CH3:1])=[C:6]12)=[O:18]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 126587009,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 142099804-chlorocarbonyl-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

8.2 g (0.036 mol) of 4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one were suspended in 365 ml of dichloromethane and after the addition of 40 ml (0.08 mol) of a 20% phosgene solution in toluene the mixture was stirred for 7 days at ambient temperature. The solution formed was washed three times, each time with 80 ml of water, dried over sodium sulphate and the solvent was eliminated in vacuo. The desired compound was freed from contaminants by column chromatography on MN silica gel 60 (70-230 mesh ASTM) using dichloromethane/ethyl acetate/petroleum ether 5/5/4 (v/v) as eluant. 6.1 g (58% of theory) of colourless crystals were obtained, m.p. 238°-239° C., RF 0.77 (Macherey-Nagel, PolygramRSIL G/UV254, pre-coated plastic sheets for TLC, eluant: dichloromethane/ethyl acetate/petroleum ether 5/5/4 v/v).

Workup

  1. customThe solution formed
  2. washwas washed three times
  3. dry with materialeach time with 80 ml of water, dried over sodium sulphate
  4. custom6.1 g (58% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-2dde770c56b84521b432f16f40f54c51
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

Loading…