Lawesson's reagent → HCID 86718511, compound

HRID 1485481Notes

Reaction equation

HRID 1485481 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][C:7](=O)[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1COCC1>[CH3:1][C:2]1([CH3:14])[CH2:8][C:7](=[S:24])[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 12206142HCID 12206142, compound

Product 1

HCID 86718511HCID 86718511, compoundYield 144.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A disposable tube was charged with 4,4-dimethyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (697 mg, 3.66 mmol) in THF (20 mL). Lawesson's Reagent (815 mg, 2.015 mmol) was added, and the solution was stirred at 80° C. for 3 h. The solution was concentrated, partitioned between water and ethyl acetate, separated, dried with sodium sulfate, concentrated with celite, and purified by silica gel chromatography to yield 4,4-dimethyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione as a yellow oily solid (0.60 g, 2.91 mmol, 79%).

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned between water and ethyl acetate
  3. customseparated
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated with celite
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-af8dd2ec25434f8fa6b98e61193d3722
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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