Lawesson's reagent → 5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepine-2(3H)-thione

HRID 1772328Notes

Reaction equation

HRID 1772328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:20]([CH3:21])=[C:19]([CH3:22])[S:18][C:10]=3[NH:11][C:12](=O)[C:13]([CH3:16])([CH3:15])[N:14]=2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:20]([CH3:21])=[C:19]([CH3:22])[S:18][C:10]=3[NH:11][C:12](=[S:32])[C:13]([CH3:16])([CH3:15])[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1363380625-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepin-2(3H)-one

Product 1

HCID 1363380635-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepine-2(3H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A round bottomed flask was charged with 5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepin-2(3H)-one (324 mg, 0.973 mmol) and a stir bar. Toluene (20 mL, 0.05 M) was added, followed by Lawesson's Reagent (217 mg, 0.535 mmol, 0.55 equiv), and the solution stirred at reflux 4 h. The solution was concentrated and purified by column chromatography (eluting with hexanes/ethyl acetate) to yield 5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepine-2(3H)-thione as a yellow amorphous solid (m/z=349) that was used in the subsequent reaction.

Workup

  1. temperatureat reflux 4 h
  2. concentrationThe solution was concentrated
  3. custompurified by column chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-0a804ff0e4c24ce5858384e2cb2b8382
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

Loading…