Toluene → HCID 19367210, compound

HRID 849502Notes

Reaction equation

HRID 849502 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=O)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1.C1(C)C=CC=CC=1>O>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]([C:7](=[S:31])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 7732993HCID 7732993, compound

Product 1

HCID 19367210HCID 19367210, compoundYield 145.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 102.4 g of 4-trifluoromethyl-2'-methoxybenzanilide prepared by the same manner as described in (1), 77.2 g of Lawesson's reagent, and 400 ml of toluene was refluxed for 1 hour. The reaction mixture was cooled to about 100° C. and then 300 ml of water was added. The resulting mixture was refluxed for 1 hour. The organic layer was separated, dried over magnesium sulfate, and concentrated to about 200 ml of volume. The precipitate was collected by filtration, washed with toluene, and dried to give 86.2 g of 4-trifluoromethyl-2'-methoxybenzothioanilide.

Workup

  1. customprepared by the same manner
  2. temperaturewas refluxed for 1 hour
  3. temperatureThe resulting mixture was refluxed for 1 hour
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to about 200 ml of volume
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with toluene
  9. customdried

Sources & evidence

ORD record
ord-66f334df2f19436483adb0f166dec9ce
Source dataset
uspto-grants-2000_01
Patent number
US06013659

Reaction notes

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