Hydrochloric Acid → 1-(2-Hydroxyethyl)-2-imidazolinethione

HRID 256540

Reaction equation

HRID 256540 reaction equation
OC[CH2:3][NH:4][CH2:5][CH2:6][NH2:7].C(=S)=[S:9].Cl.[CH2:12]([OH:14])[CH3:13].O>>[OH:14][CH2:12][CH2:13][N:4]1[CH2:5][C:6](=[S:9])[N:7]=[CH:3]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon Disulfide3×HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 19096565Water ethanol

Product 1

HCID 197853781-(2-Hydroxyethyl)-2-imidazolinethione

Procedure

(Hydroxyethyl)ethylenediamine (25 ml) is dissolved in 1:1 ethyl alcohol-water (85 mL) and heated to 40°-50° C. Carbon disulfide (16.5 ml) is added dropwise over a period of about 15 minutes. After about half of the amount is added, the exothermic reaction starts and the reaction mixture solidifies. After the addition of all of the carbon disulfide, the mixture is refluxed gently for about 1 hour. Concentrated hydrochloric acid (2 ml) is then added and the reaction mixture is refluxed overnight. The solid which separates after the addition of carbon disulfide redissolves. The solution is cooled in an ice bath, and the solid separates, is filtered out, washed well with isopropyl alcohol and t-butyl methyl ether and dried to give 23.3 g of 1-(2-hydroxyethyl)-2-imidazolinethione, melting point 137°-138° C.

Workup

  1. temperatureheated to 40°-50° C
  2. additionAfter about half of the amount is added
  3. customthe exothermic reaction starts
  4. temperaturethe mixture is refluxed gently for about 1 hour
  5. temperaturethe reaction mixture is refluxed overnight
  6. dissolutionredissolves
  7. temperatureThe solution is cooled in an ice bath
  8. filtrationthe solid separates, is filtered out
  9. washwashed well with isopropyl alcohol and t-butyl methyl ether
  10. customdried

Sources & evidence

ORD record
ord-eedbe9a592fe4d859221132b42e65042
Source dataset
uspto-grants-1993_11
Patent number
US05258381

Linked notes

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