HCID 14839440, compound → HCID 15027408, compound

HRID 1090820Notes

Reaction equation

HRID 1090820 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[N:3]=1.Cl.[CH3:12][NH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl>C(O)C>[CH3:12][NH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][S:1][C:2]1[NH:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14839440HCID 14839440, compoundHCID 1785278154,5,6,7-tetrahydro-1H-benzimidazole-2-thiol

Product 1

HCID 15027408HCID 15027408, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1.3 g (9 mmol) of 2-mercapto-4,5,6,7-tetrahydro-1H-benzimidazole in 20 ml of ethanol was added 1.35 g (7 mmol) of 2-methylaminobenzyl chloride hydrochloride for a period of 15 min. The solvent was distilled off, and the residue was shaken sufficiently with a combination of 1N aqueous sodium hydroxide and chloroform for performing extraction. The organic portion was taken out and then dried over anhydrous sodium sulfate. Chloroform was distilled off, and the residue was crystallized from ether/hexane to give 1.02 g of the desired compound as a pale brown crystalline product, yield 53%.

Workup

  1. distillationThe solvent was distilled off
  2. extractionextraction
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationChloroform was distilled off
  5. customthe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-84c8fc1fd55f48a6b03bcf4b7d80b76c
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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