2-(Chloromethyl)aniline--hydrogen chloride (1/1) → 2-(2-Aminobenzylthio)imidazole

HRID 1090829Notes

Reaction equation

HRID 1090829 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl.[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Cl>C(O)C>[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][S:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178527877HCID 178527877, compound

Product 1

HCID 150274202-(2-Aminobenzylthio)imidazoleYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.5 g (15 mmol) of 2-mercaptoimidazole in 15 ml of ethanol was added at room temperature 2.66 g (15 mmol) of 2-aminobenzyl chloride hydrochloride. The mixture was then stirred for one hr. at room temperature. The obtained homogeneous solution was placed under reduced pressure at a temperature below 40° C. to distill off the solvent. To the residue were successively added water and saturated aqueous sodium hydrogencarbonate to precipitate a crystalline product. The product was collected by filtration, washed twice with water, and dried to give 2.5 g of the desired compound as a pale gray crystalline product, yield 80.9%.

Workup

  1. customat room temperature
  2. customwas placed under reduced pressure at a temperature below 40° C.
  3. distillationto distill off the solvent
  4. customto precipitate a crystalline product
  5. filtrationThe product was collected by filtration
  6. washwashed twice with water
  7. customdried

Sources & evidence

ORD record
ord-4a1dcffda9f544599cc9fd18e9fb909d
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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