Lawesson's reagent → UC-781

HRID 50017Notes

Reaction equation

HRID 50017 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=O)=[CH:4][C:3]=1[O:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21].C(=O)(O)[O-].[Na+].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=[S:37])=[CH:4][C:3]=1[O:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 471850N-[4-chloro-3-(3-methyl-2-butenyloxy)phenyl]-2-methyl-3-furancarboxamideHCID 516892Sodium Bicarbonate

Product 1

HCID 3000926UC-781

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A reaction mixture of N-[4-chloro-3-(3-methyl-2-butenyloxy)phenyl]-2-methyl-3-furancarboxamide (4 g), sodium bicarbonate (7.4 g) and Lawesson's reagent (3.6 g) in toluene (168 mL) was gradually heated to 85° C. over 1½ hours and then held at this temperature for a further 2½ hours. The reaction mixture was then cooled and filtered through a plug of neutral aluminum oxide and eluted with ether:petroleum ether (1:1). Evaporation of the solvent gave the product, N-[4-chloro-3-(3-methyl-2-butenyloxy)phenyl]-2-methyl-3-furancarbothioamide, 2.6 g.

Workup

  1. waitheld at this temperature for a further 2½ hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered through a plug of neutral aluminum oxide
  4. washeluted with ether:petroleum ether (1:1)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-438be4fdd95c487ab853e0ee1068d696
Source dataset
uspto-grants-2004_03
Patent number
US06710077B1

Reaction notes

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