O-Xylene → 3,4-Dimethylbenzene-1-carbothioamide

HRID 436310Notes

Reaction equation

HRID 436310 reaction equation
[S-:1][C:2]#[N:3].[K+].[CH3:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[CH3:12].F>>[CH3:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:2]([NH2:3])=[S:1]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 14917Hydrofluoric AcidHCID 516872Potassium thiocyanate

Product 1

HCID 204708513,4-Dimethylbenzene-1-carbothioamide

Procedure

At a temperature as indicated in Example 1, 59 g of potassium thiocyanate (0.6 mol) and 79.5 g of o-xylene (0.75 mol) are stirred with 0.5 l of 98% hydrofluoric acid. and the mixture is then stirred for 10 hours at room temperature. Subsequently, the batch is poured onto ice, the precipitated product is suction-filtered after having been stirred for one-half hour, and the greater part of the non-reacted o-xylene (15 g) is separated from the still moist filter cake by steam distillation. The distillation residue is subsequently suction-filtered and dried. The yield of dimethylthiobenzamide having a melting point of 120° - 125° C is 99 g and therefore quantitative, relative to the potassium thiocyanate used.

Workup

  1. additionSubsequently, the batch is poured onto ice
  2. filtrationthe precipitated product is suction-filtered
  3. stirringafter having been stirred for one-half hour
  4. customthe greater part of the non-reacted o-xylene (15 g) is separated from the still moist filter cake by steam distillation
  5. filtrationThe distillation residue is subsequently suction-filtered
  6. customdried

Sources & evidence

ORD record
ord-97dcba008f2441af99e13f908a27b9ec
Source dataset
uspto-grants-1977_02
Patent number
US04008264

Reaction notes

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