Toluene → HCID 86596038, compound

HRID 2353364Notes

Reaction equation

HRID 2353364 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=O)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1.C1(C)C=CC=CC=1>CCOCC>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[S:31])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 684512324-Chloro-N-(4-methylphenyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 86596038HCID 86596038, compoundYield 153.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

4-chloro-N-p-tolyl-3-trifluoromethyl-benzamide (1.0 g, 3.19 mmol), Lawesson's reagent (774 mg, 0.6 eq.) and toluene (2.5 mL) is mixed in a microwave vial. The mixture is heated to 120° C. for 1000 seconds using microwave irradiation. The mixture turned into clear solution. Ether (50 ml) is added to dilute the reaction mixture. The solution is then washed with brine, dried over MgSO4, filtered and concentrated. The mixture is purified by column chromatography (EtOAc/Hexanes=5/95) to afford 970 mg (92%) of 4-chloro-N-p-tolyl-3-trifluoromethyl-thiobenzamide as a yellow solid.

Workup

  1. custommicrowave irradiation
  2. additionto dilute the reaction mixture
  3. washThe solution is then washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe mixture is purified by column chromatography (EtOAc/Hexanes=5/95)

Sources & evidence

ORD record
ord-297527f12e0a481baa5bee39ffd26656
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

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