Ammonia → HCID 20460601, compound

HRID 543707Notes

Reaction equation

HRID 543707 reaction equation
N.C[Si](C)(C)Cl.[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1.[CH:16]1([S:22]Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C1(C)C=CC=CC=1.CCCCC>[CH:16]1([S:22][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 5798BenzimidazoleHCID 6397ChlorotrimethylsilaneHCID 87312Cyclohexanesulfenyl chloride

Product 1

HCID 20460601HCID 20460601, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8003PentaneSolvent

Procedure

NH3 gas was passed into 80.4 g of trimethylchlorosilane in 500 ml of dry toluene at 50° to 60° C. to saturation. 59.1 g of benzimidazole were then added and the mixture was boiled for 10 hours under reflux. To remove excess ammonia, 250 ml of toluene were distilled off in vacuo, and 0.5 mol of cyclohexylsulphenyl chloride in 500 ml of pentane was then added dropwise. The mixture was subsequently stirred for 4 hours and filtered, and the solvent was removed in vacuo. 99 g of 1-cyclohexylthiobenzimidazole were obtained as a red-brown oil.

Workup

  1. temperatureunder reflux
  2. customTo remove excess ammonia, 250 ml of toluene
  3. additionwas then added dropwise
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4fc8cbcf379b42d8964da9f08e4b1e97
Source dataset
uspto-grants-1984_05
Patent number
US04447440

Reaction notes

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