Lawesson's reagent → HCID 89717812, compound

HRID 1504934Notes

Reaction equation

HRID 1504934 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:27][C:28](=[O:42])[NH:29][CH2:30][C:31](=O)[NH:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=1[F:40])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([O:27][C:28](=[O:42])[NH:29][CH2:30][C:31](=[S:10])[NH:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=1[F:40])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 84480946HCID 84480946, compound

Product 1

HCID 89717812HCID 89717812, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A Lawesson's reagent (50 mg, 0.12 mmol) was added to a THF (2 mL) solution of [(2,6-difluorophenylcarbamoyl)methyl]carbamic acid tert-butyl ester (52 mg, 0.18 mmol) in an argon atmosphere, and the mixture was refluxed with heating overnight. After evaporating the solvent, the residue was purified by silica gel column chromatography (13 g, hexane:acetone=10:1 to 8:1) to obtain [(2,6-difluorophenylthiocarbamoyl)methyl]carbamic acid tert-butyl ester (23 mg) as a colorless crystalline substance.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating overnight
  3. customAfter evaporating the solvent
  4. customthe residue was purified by silica gel column chromatography (13 g, hexane:acetone=10:1 to 8:1)

Sources & evidence

ORD record
ord-dce69e4d4acc48eead9b1f8d877b2c3e
Source dataset
uspto-grants-2015_12
Patent number
US09216954B2

Reaction notes

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