Ethyl isothiocyanate → HCID 178465516, compound

HRID 2398330Notes

Reaction equation

HRID 2398330 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[CH2:12]([N:14]=[C:15]=[S:16])[CH3:13]>C(O)C>[CH2:12]([NH:14][C:15]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:6]1[NH:5][CH:4]=[N:3][C:2]=1[CH3:1])=[S:16])[CH3:13]

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 178433288HCID 178433288, compound

Product 1

HCID 178465516HCID 178465516, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous ethylamine (9.0 g.) was added to a solution of N-cyano-N'[2-((4-methyl-5-imidazolyl)methylthio)ethyl]S-methylisothiourea (Example 3(c), 5.0 g.) in ethanol. The solution was heated under reflux for 8 hours and concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol, filtered, and diluted with water. The white solid obtained was recrystallised from isopropyl alcohol-ether to yield N-cyano-N'-ethyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine, m.p. 118°-120°. (Found: C, 49.6; H, 6.8; N, 31.2; S, 11.7. C11H18N6S requires: C, 49.6; H, 6.8; N, 31.6; S, 12.0). (b) (i) A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole (6.9 g.) and ethyl isothiocyanate (3.84 g.) in ethanol was heated under reflux for 2 hours. Concentration followed by recrystallisation of the residue from aqueous ethanol gave N-ethyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea (9.0 g.), m.p. 140°-141°. (Found: C, 46.5; H, 7.1; N, 21.7; S, 25.1. C10H18N4S2 requires: C, 46.5; H, 7.0; N, 21.7; S, 24.8).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationConcentration
  3. customfollowed by recrystallisation of the residue from aqueous ethanol

Sources & evidence

ORD record
ord-eefde511ed52439bbad555b62be50514
Source dataset
uspto-grants-1977_05
Patent number
US04024271

Reaction notes

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