Lawesson's reagent → HCID 86239860, compound

HRID 1664866Notes

Reaction equation

HRID 1664866 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH2:23]([CH:26]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[F:40])[CH2:29][NH:28][C:27]1=O)[CH:24]=[CH2:25]>C1(C)C=CC=CC=1>[CH2:23]([CH:26]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[F:40])[CH2:29][NH:28][C:27]1=[S:10])[CH:24]=[CH2:25]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59722656HCID 59722656, compound

Product 1

HCID 86239860HCID 86239860, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (649 mg, 1.61 mmol) was added to a suspension 3-allyl-6-(2,3-difluorophenyl)azepan-2-one (426 mg, 1.61 mmol) in toluene (10 mL). After 3 h, the reaction mixture was heated to 45° C. After 30 min, the mixture was concentrated in a cold water bath. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (257 mg). MS 282.1 (M+1).

Workup

  1. waitAfter 30 min
  2. concentrationthe mixture was concentrated in a cold water bath
  3. customPurification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8c7e53a7e314439d9a3080274a081777
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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