Toluene → HCID 21712145, compound

HRID 650498Notes

Reaction equation

HRID 650498 reaction equation
[CH2:1]([N:8]1[C:13]([C:14]2[C:18]([Cl:19])=[C:17]([O:20][CH:21]([F:23])[F:22])[N:16]([CH3:24])[N:15]=2)=[C:12]([F:25])[CH:11]=[C:10]([Cl:26])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>C(Cl)Cl>[CH2:1]([N:8]1[C:13]([C:14]2[C:18]([Cl:19])=[C:17]([O:20][CH:21]([F:23])[F:22])[N:16]([CH3:24])[N:15]=2)=[C:12]([F:25])[CH:11]=[C:10]([Cl:26])[C:9]1=[S:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 21712164HCID 21712164, compound

Product 1

HCID 21712145HCID 21712145, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

0.50 g of 1-benzyl-3-chloro-6-(4-chloro-5-difluoromethoxy-1-methyl-[1H]-pyrazol-3-yl)-5-fluoro-[1H]-pyridin-2-one is introduced into 5 ml of toluene, 0.63 g of Lawesson's reagent is added and the resulting yellow suspension is stirred overnight at 120° C. The next day, the mixture is cooled to 22° C., diluted with methylene chloride and, after the addition of 3 g of silica gel, concentrated to dryness in vacuo. The silica gel is applied to a flash chromatography column and eluted first with toluene/ethyl acetate 30/1 (v/v) and then with n-hexane/ethyl acetate 2/1 (v/v). 0.32 g of the desired title compound is obtained in the form of a yellow solid having a melting point of 135-138° C.

Workup

  1. additionis added
  2. temperatureThe next day, the mixture is cooled to 22° C.
  3. additionafter the addition of 3 g of silica gel
  4. concentrationconcentrated to dryness in vacuo
  5. washeluted first with toluene/ethyl acetate 30/1 (v/v)

Sources & evidence

ORD record
ord-6e33a53eafe8469d82c7a10cd1049adc
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Reaction notes

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