Cysteamine Hydrochloride → 2-((Thiophen-2-ylmethyl)thio)ethan-1-amine

HRID 1719146Notes

Reaction equation

HRID 1719146 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].O[CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.[OH-].[Na+]>Cl>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[CH2:7][S:5][CH2:4][CH2:3][NH2:2]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 694672-Thiophenemethanol

Product 1

HCID 49622502-((Thiophen-2-ylmethyl)thio)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(b)(i) Cysteamine hydrochloride (9.95 g) was dissolved in concentrated hydrochloric acid (50 ml) and the solution was cooled to 0°. 2-Hydroxymethylthiophene (10 g) was added dropwise to the stirred solution which was maintained at below 5°. The mixture was stirred overnight at room temperature, adjusted to pH 10 with concentrated aqueous sodium hydroxide and extracted with ethyl acetate. The extracts were evaporated and the residue was distilled at 158°-164°/760 mm Hg to give 2-(2-thienylmethylthio)ethylamine which was converted into the hydrochloride, m.p. 108°-111°, by treatment with ethanolic HCl and ether.

Workup

  1. temperaturethe solution was cooled to 0°
  2. temperaturewas maintained at below 5°
  3. extractionextracted with ethyl acetate
  4. customThe extracts were evaporated
  5. distillationthe residue was distilled at 158°-164°/760 mm Hg

Sources & evidence

ORD record
ord-11f1069b229f4f17be6c07d04ee88e61
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

Loading…