Lawesson's reagent → HCID 21059932, compound

HRID 1241445Notes

Reaction equation

HRID 1241445 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Si:23]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([NH2:47])=O)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1C=CC=CC=1>[Si:23]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45](=[S:10])[NH2:47])([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 21059931HCID 21059931, compound

Product 1

HCID 21059932HCID 21059932, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Lawesson's reagent (8.19 g, 20.25 mmol) was heated to reflux in benzene (100 mL) for 1 hr. Cool to just below reflux temperature, and add a solution of 5-{[tert-butyl(diphenyl)silyl]oxy}pentanamide (7.20 g, 20.25 mmol in 50 mL benzene). Stir at room temperature for 2 hrs. Concentrate in vacuo to a chunky oil and purified via silica gel chromatography (eluent: 9:1 Hexane:Ethyl Acetate) to give the product as a yellow-green oil. Yield: 6.50 g (62%) 1H NMR (DMSO-d6) δ7.65–7.60 (m, 4H), 7.49–7.41 (m, 6H), 3.68–3.63 (t, 2H), 2.50–2.44 (t, 2H), 1.80–1.70 (m, 2H), 1.60–1.51 (m, 2H), 1.00 (s, 9H).

Workup

  1. temperatureCool to just
  2. temperaturebelow reflux temperature
  3. concentrationConcentrate in vacuo to a chunky oil
  4. custompurified via silica gel chromatography (eluent: 9:1 Hexane:Ethyl Acetate)

Sources & evidence

ORD record
ord-0b02962ccd6a43cbbff183e668e4d1ce
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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