2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 15027412, compound

HRID 1090823Notes

Reaction equation

HRID 1090823 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.[NH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl>C(O)C>[NH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][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 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 1785278154,5,6,7-tetrahydro-1H-benzimidazole-2-thiol

Product 1

HCID 15027412HCID 15027412, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1.5 g (purity 75%, 7.3 mmol) of 2-mercapto-4,5,6,7-tetrahydro-1H-benzimidazole in 15 ml of ethanol was added 1.3 g (7.3 mmol) of 2-aminobenzyl chloride hydrochloride, and the mixture was stirred for 2 hrs. at room temperature. Ethanol was distilled off under reduced pressure at room temperature. The residue was made alkaline by addition of saturated aqueous sodium hydrogencarbonate and then extracted with 40 ml of chloroform. The chloroform portion was washed with 10 ml of 0.2N NaOH and then with saturated aqueous sodium chloride. The washed chloroform portion was dried over anhydrous sodium sulfate and placed under reduced pressure to distill off the solvent. The residue was purified by silica gel column chromatography using chloroform-methanol to give 1.35 g of the desired compound as a pale yellow oil, yield 71.4%.

Workup

  1. customat room temperature
  2. distillationEthanol was distilled off under reduced pressure at room temperature
  3. additionby addition of saturated aqueous sodium hydrogencarbonate
  4. extractionextracted with 40 ml of chloroform
  5. washThe chloroform portion was washed with 10 ml of 0.2N NaOH
  6. dry with materialThe washed chloroform portion was dried over anhydrous sodium sulfate
  7. distillationto distill off the solvent
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6503b9f0bbfc4902a853283e162e806b
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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