Lawesson's reagent → HCID 14510214, compound

HRID 1709750Notes

Reaction equation

HRID 1709750 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=O.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][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[S:26]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9413884HCID 9413884, compound

Product 1

HCID 14510214HCID 14510214, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(2-fluorophenyl)-2-pyridinecarboxamide (11.81 g, 55 mmol) was reacted with Lawesson's reagent (26.04 g, 64 mmol) in toluene (160 mL) at reflux temperature for 5 hours. The solution was preadsorbed onto silica gel and flash chromatographed (eluted with 2.5% ethyl acetate in petroleum ether) to give N-(2-fluorophenyl)-2-pyridinecarbothioamide as a yellow solid (7.26 g, 39%) m.p. 94°-97° C.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customchromatographed
  3. wash(eluted with 2.5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2375028446e047caa0eb63e31df12b6a
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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