Lawesson's reagent → HCID 14510216, compound

HRID 1709747Notes

Reaction equation

HRID 1709747 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[S:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 2653165HCID 2653165, compound

Product 1

HCID 14510216HCID 14510216, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(4-fluorophenyl)-2-pyridinecarboxamide (11.47 g, 53.0 mmol) and Lawesson's reagent (25.75 g, 63.7 mmol) were refluxed in toluene for 6.5 hours, preadsorbed onto silica gel, and flash chromatographed (500 g of silica gel eluted with 15% ethyl acetate in petroleum ether) affording N-(4-fluorophenyl)-2-pyridinecarbothioamide as a yellow solid (6.60 g, 54%) m.p. 82°-85° C.

Workup

  1. customchromatographed
  2. wash(500 g of silica gel eluted with 15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f0751e5dda4743a5a2a61ced5d0264c9
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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