Water → N-(2-Methoxyphenyl)-4-methylbenzenecarbothioamide

HRID 1165477Notes

Reaction equation

HRID 1165477 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6](=[S:28])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 774520HCID 774520, compound2×

Product 1

HCID 10422598N-(2-Methoxyphenyl)-4-methylbenzenecarbothioamideYield 108.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

The 4-methyl-2'-methoxybenzanilide (50.0 g) obtained in (1) was dissolved in 200 ml of toluene, and 46.1 g of Lawesson's reagent was added. The mixture was refluxed for 1 hour. After the reaction, the reaction mixture was cooled to about 50° C., and 200 ml of water was added. The mixture was further refluxed for 2 hours. The organic layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was evapoated under reduced pressure. The residue was recrystallized from methanol and then cyclohexane to give 31.9 g of 4-methyl-2'-methoxybenzothioanilide. mp 91.0°-93.0° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customAfter the reaction
  3. temperatureThe mixture was further refluxed for 2 hours
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-0408812b488047f28cd396d43767ce22
Source dataset
uspto-grants-1990_03
Patent number
US04910211

Reaction notes

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