Lawesson's reagent → HCID 135415188, compound

HRID 620182Notes

Reaction equation

HRID 620182 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[C:18]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)[S:17][C:10]=2[NH:11][C:12](=O)[CH:13]([CH3:15])[N:14]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[C:18]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)[S:17][C:10]=2[NH:11][C:12](=[S:41])[CH:13]([CH3:15])[N:14]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 135467864HCID 135467864, compound

Product 1

HCID 135415188HCID 135415188, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2 g of 5-(2-chlorophenyl)-7-[2-(4-isobutylphenyl)ethyl]-3-methyl-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepin-2-one, melting at 188°-191° C. and 1.04 g of Lawesson reagent in 37 ml of toluene is stirred at 40°-45° C. for an hour. The resultant solution is concentrated under reduced pressure, and the residue is subjected to chromatography on silica gel and then eluted with chloroform-methanol (100:1 to 100:2). The objective fraction is concentrated under reduced pressure to give 1.2 g of 5-(2-chlorophenyl)-7-[2-(4-isobutylphenyl)ethyl]-3-methyl-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione.

Workup

  1. concentrationThe resultant solution is concentrated under reduced pressure
  2. washeluted with chloroform-methanol (100:1 to 100:2)
  3. concentrationThe objective fraction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-740374aff52849bba2cc85493198380a
Source dataset
uspto-grants-1989_04
Patent number
US04820703

Reaction notes

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