Methanol → HCID 178433691, compound

HRID 2412561Notes

Reaction equation

HRID 2412561 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH:9]([C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][N:22]=[C:23]=[S:24])[N:17]=1)[C:10]([NH2:12])=[NH:11].C(N(CC)CC)C.[CH3:32][C:33]1[NH:37][CH:36]=[N:35][C:34]=1[CH2:38][S:39][CH2:40][CH2:41][NH2:42].CO>O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH:9]([C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][NH:22][C:23]([NH:42][CH2:41][CH2:40][S:39][CH2:38][C:34]2[N:35]=[CH:36][NH:37][C:33]=2[CH3:32])=[S:24])[N:17]=1)[C:10]([NH2:12])=[NH:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 178512725HCID 178512725, compound

Product 1

HCID 178433691HCID 178433691, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-guanidinothiazol-4-ylmethylthio)ethyl isothiocyanate hydrogen maleate (0.778 g), triethylamine (1.0 g), 5-methyl-4-[(2-aminoethyl)thiomethyl]imidazole (0.364 g) and methanol (20 ml) was stirred at room temperature overnight. The mixture was poured into water (60 ml), extracted with ethyl acetate (2×50 ml), the combined extracts washed with water (25 ml), dried (MgSO4), filtered and evaporated to dryness. The residue was dissolved in acetone (10 ml) and added to a solution of maleic acid (0.28 g) in acetone (10 ml). The precipitate was filtered off and recrystallized from ethanol (charcoal) to give 1-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]-3-[2-(5-methylimidazol-4-ylmethylthio)ethyl]thiourea maleate as a white solid, m.p. 90°-93° (decomp.).

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. washthe combined extracts washed with water (25 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in acetone (10 ml)
  7. additionadded to a solution of maleic acid (0.28 g) in acetone (10 ml)
  8. filtrationThe precipitate was filtered off
  9. customrecrystallized from ethanol (charcoal)

Sources & evidence

ORD record
ord-6f5716d16cba43e4819a09d1c2c37aa8
Source dataset
uspto-grants-1985_01
Patent number
US04493840

Reaction notes

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