Triethylamine → HCID 178512726, compound

HRID 2412560Notes

Reaction equation

HRID 2412560 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].Cl.Cl.[NH2:27][CH2:28][CH2:29][C:30]1[N:31]=[CH:32][NH:33][CH:34]=1.C(N(CC)CC)C>CO>[OH2:5].[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[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:27][CH2:28][CH2:29][C:30]2[N:31]=[CH:32][NH:33][CH:34]=2)=[S:24])[N:17]=1)[C:10]([NH2:12])=[NH:11].[NH:9]([C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][NH:22][C:23]([NH:27][CH2:28][CH2:29][C:30]2[N:31]=[CH:32][NH:33][CH:34]=2)=[S:24])[N:17]=1)[C:10]([NH2:12])=[NH:11].[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178478691HCID 178478691, compoundHCID 178512725HCID 178512725, compound

Product 1

HCID 178512726HCID 178512726, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-guanidinothiazol-4-ylmethylthio)ethyl isothiocyanate hydrogen maleate (0.712 g), 4-(2-aminoethyl)imidazole dihydrochloride (histamine dihydrochloride) (0.404 g), triethylamine (0.808 g) and methanol (35 ml) was stirred at room temperature overnight. The mixture was purified by preparative thin layer chromatography on Merck 60 F-254 plates using as solvent ethyl acetate/ethanol/ammonia (s.g. 0.88) 6:1:1 v/v/v, eluting the band of RF 0.4 from the plates with ethanol. Evaporation of the filtered extract followed by treatment with maleic acid in acetone gave a white solid which was filtered off and washed with acetone followed by a little cold ethanol to give 1-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]-3-[2-(imidazol-4-yl)ethyl]thiourea dimaleate hemihydrate, m.p. 100° C. (decomp.).

Workup

  1. customThe mixture was purified by preparative thin layer chromatography on Merck 60 F-254 plates
  2. washeluting the band of RF 0.4 from the plates with ethanol
  3. customEvaporation of the filtered
  4. extractionextract
  5. customgave a white solid which
  6. filtrationwas filtered off
  7. washwashed with acetone

Sources & evidence

ORD record
ord-6003ef05347f424eb19db076833e6782
Source dataset
uspto-grants-1985_01
Patent number
US04493840

Reaction notes

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