Triethylamine → HCID 178486119, compound

HRID 67978Notes

Reaction equation

HRID 67978 reaction equation
Cl.[NH:2]([C:6]1[S:7][CH:8]=[C:9]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[N:10]=1)[C:3]([NH2:5])=[NH:4].C(N(CC)CC)C.[CH3:23][N:24]=[C:25]=[S:26].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>CO.CC(C)=O>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[NH:2]([C:6]1[S:7][CH:8]=[C:9]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:25]([NH:24][CH3:23])=[S:26])[N:10]=1)[C:3]([NH2:5])=[NH:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 444266Maleic AcidHCID 178479416HCID 178479416, compound

Product 1

HCID 178486119HCID 178486119, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 887MethanolSolvent

Procedure

A suspension of 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole hydrochloride (1.52 g.) in methanol (30 ml.) was treated with triethylamine (1.01 g.) to give a pale yellow solution. Methyl isothiocyanate (0.365 g.) was added and the solution stirred for 16 hours at room temperature. Evaporation of the solvent gave a gum which was dissolved in acetone (20 ml.) and treated with maleic acid (1 g.) in acetone (20 ml.). The precipitate was filtered off and recrystallized from ethanol to give 2-guanidino-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole hydrogen maleate as a pale brown solid (0.420 g.). Found: C, 37.4; H, 4.7; N, 19.8; S, 22.7. C13H20N6S3O4 requires C, 37.14; H, 4.76; N, 20.00; S, 22.85%.

Workup

  1. customto give a pale yellow solution
  2. customEvaporation of the solvent
  3. customgave a gum which
  4. filtrationThe precipitate was filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b5d658044a8749658f93d82fcbc613f6
Source dataset
uspto-grants-1982_08
Patent number
US04347370

Reaction notes

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