Lawesson's reagent → HCID 86718492, compound

HRID 1485385Notes

Reaction equation

HRID 1485385 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=O)[CH2:8][CH2:9][NH:10][C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[S:23])[CH2:8][CH2:9][NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 105380607-Bromo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

Product 1

HCID 86718492HCID 86718492, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-bromo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (3) (1.5 g, 6.25 mmol) and Lawesson's Reagent (2.5 g, 12.5 mmol) in THF (50 mL) was heated at 80° C. overnight. The mixture was evaporated, water (50 mL) was added and the solution was extracted with ethyl acetate (100 mL), washed with water (50 mL), dried and concentrated to give the residue, which was purified by CombiFlash (PE:EA=5:1) to afford 7-bromo-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (1.2 g, yield 75%). LRMS (M+H)+: 256 m/z. 1H NMR (300 MHz, CDCl3) δ 3.13-3.17 (t, J=5.4 Hz, 2H), 3.75-3.79 (t, J=5.4 Hz, 2H), 6.77-6.80 (m, 1H), 6.95-6.98 (m, 2H).

Workup

  1. customThe mixture was evaporated
  2. additionwater (50 mL) was added
  3. extractionthe solution was extracted with ethyl acetate (100 mL)
  4. washwashed with water (50 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto give the residue, which
  8. customwas purified by CombiFlash (PE:EA=5:1)

Sources & evidence

ORD record
ord-cfd4445275c7452cb864cacc52492267
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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