Triethylamine → HCID 178512726, compound

HRID 1105599Notes

Reaction equation

HRID 1105599 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-10b6370e7b51463f8b80a3e6f0977f4c
Source dataset
uspto-grants-1982_01
Patent number
US04309435

Reaction notes

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