Methyl isothiocyanate → HCID 21432765, compound

HRID 2399120Notes

Reaction equation

HRID 2399120 reaction equation
[NH2:1][C:2]1[C:3]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][N:20]=[C:21]=[S:22]>C(O)C>[CH3:19][NH:20][C:21]([NH:12][CH2:11][CH2:10][S:9][CH2:8][C:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[S:22]

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 11430Potassium CarbonateHCID 12951533HCID 12951533, compound

Product 1

HCID 21432765HCID 21432765, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-2-[(2-aminoethyl)thiomethyl]pyridine (3.0 g,) prepared from an aqueous slurry of the dihydrobromide and potassium carbonate, by extraction with ethanol-ether (2:1) was dissolved in ethanol (25 ml.), methyl isothiocyanate (1.16 g.) added, and the solution then heated under reflux for 30 minutes. The residue was triturated with ether affording a solid (3.4 g.) m.p. 98°-100°. Recrystallisation from isopropyl acetate gave N-methyl-N'-[2-((3-amino-2-pyridyl)methylthio)ethyl]thiourea in 3 crops, m.p. 99.5°-100.5 (1.33 g.), m.p. 100°-101° (1.04 g.) and m.p. 99°-100° (1.0 g.).

Workup

  1. temperaturethe solution then heated
  2. temperatureunder reflux for 30 minutes
  3. customThe residue was triturated with ether affording a solid (3.4 g.) m.p. 98°-100°
  4. customRecrystallisation from isopropyl acetate

Sources & evidence

ORD record
ord-0c5d2882409d426c9e817761cc657444
Source dataset
uspto-grants-1977_05
Patent number
US04027026

Reaction notes

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