Cyanogen Chloride → 2-thiocyanato-benzoic acid N-(3,5,5-trimethylcyclohexyl)-amide

HRID 1285146Notes

Reaction equation

HRID 1285146 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[SH:18])[CH2:3]1.[N:20]#[C:21]Cl>O1CCCC1>[CH3:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][C:21]#[N:20])[CH2:3]1

Participants

4

Reactant 2

HCID 10477Cyanogen ChlorideHCID 135039612-mercaptobenzoic acid N-(3,5,5-trimethyl-cyclohexyl)-amide

Product 1

HCID 135039652-thiocyanato-benzoic acid N-(3,5,5-trimethylcyclohexyl)-amideYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

49.9 g (0.18 mol) of 2-mercaptobenzoic acid N-(3,5,5-trimethyl-cyclohexyl)-amide are initially introduced into 200 ml of tetrahydrofuran. The solution is cooled to -15° C. and 33.3 g (0.54 mol) of cyanogen chloride, dissolved in 50 ml of tetrahydrofuran, are added dropwise in the course of 30 minutes such that the internal temperature does not exceed -5° C. When the dropwise addition has ended, the mixture is allowed to come to room temperature in the course of 1 hour and stirring is then continued at this temperature for a further 2 hours. Excess cyanogen chloride and some of the solvent are distilled off under reduced pressure. The solution is poured into water, with vigorous stirring, and the solid which has precipitated is filtered off with suction and dried in a desiccator. 47 g (86.5% of theory) of 2-thiocyanato-benzoic acid N-(3,5,5-trimethylcyclohexyl)-amide are obtained as a colorless powder of melting point 117° C.

Workup

  1. additionare added dropwise in the course of 30 minutes such that the internal temperature
  2. customdoes not exceed -5° C
  3. additionWhen the dropwise addition
  4. customto come to room temperature in the course of 1 hour
  5. distillationExcess cyanogen chloride and some of the solvent are distilled off under reduced pressure
  6. additionThe solution is poured into water, with vigorous stirring
  7. customthe solid which has precipitated
  8. filtrationis filtered off with suction
  9. customdried in a desiccator

Sources & evidence

ORD record
ord-298bddfa3f4349dba27ac7936e4cb3e9
Source dataset
uspto-grants-1986_01
Patent number
US04565829

Reaction notes

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