Lawesson's reagent → HCID 86718508, compound

HRID 1485470Notes

Reaction equation

HRID 1485470 reaction equation
[F:1][C:2]1[C:7]2[NH:8][C:9](=O)[CH2:10][CH2:11][NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1COCC1>[F:1][C:2]1[C:7]2[NH:8][C:9](=[S:23])[CH2:10][CH2:11][NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 79290409HCID 79290409, compound

Product 1

HCID 86718508HCID 86718508, compoundYield 180.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A disposable tube was charged with 9-fluoro-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (0.037 g, 0.205 mmol) and THF. Lawesson's Reagent (45.7 mg, 0.113 mmol) was added, and the solution was stirred at 80° C. 1 h. The mixture was concentrated, partitioned between water and ethyl acetate, separated, dried with sodium sulfate, concentrated with celite, and purified by silica gel chromatography (eluting with hexanes/ethyl acetate) to yield 9-fluoro-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione as an off-white amorphous solid (0.040 g, 0.204 mmol, 99%).

Workup

  1. custom1 h
  2. concentrationThe mixture was concentrated
  3. custompartitioned between water and ethyl acetate
  4. customseparated
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated with celite
  7. custompurified by silica gel chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-0622e35ce753463196f2743d8e35058d
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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