Triethylamine → HCID 178512719, compound

HRID 1105601Notes

Reaction equation

HRID 1105601 reaction equation
[C:1]([NH:9][C:10]([NH:12][CH2:13][CH2:14][S:15][CH2:16][C:17]1[N:18]=[C:19]([NH:22][C:23]([NH2:25])=[NH:24])[S:20][CH:21]=1)=S)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[NH2:28][CH2:29][CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1.C(N(CC)CC)C>[N+]([O-])([O-])=O.[Ag+].CN(C)C=O>[C:1]([NH:9][C:10]([NH:28][CH2:29][CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[N:12][CH2:13][CH2:14][S:15][CH2:16][C:17]1[N:18]=[C:19]([NH:22][C:23]([NH2:25])=[NH:24])[S:20][CH:21]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 178478691HCID 178478691, compoundHCID 178512727HCID 178512727, compound

Product 1

HCID 178512719HCID 178512719, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-benzoyl-3-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]thiourea (0.394 g), histamine dihydrochloride (0.276 g), triethylamine (0.20 g), silver nitrate (0.204 g) and dimethyl formamide (20 ml) was stirred at room temperature overnight. After filtration the solution was evaporated to dryness and the residue purified by preparative thin layer chromatography (Merck 60F-254 plates developed with ethyl acetate/ethanol/ammonia (s.g. 0.88) 6:1:1 v/v/v). Isolation of the main band (RF 0.3) gave an oil which crystallized on trituration with acetone to give 1-benzoyl-2-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]-3-[2-(imidazol-4-yl)ethyl]guanidine, decomposing at 147°-150° after softening at 115°-117°.

Workup

  1. filtrationAfter filtration the solution
  2. customwas evaporated to dryness
  3. customthe residue purified by preparative thin layer chromatography (Merck 60F-254 plates developed with ethyl acetate/ethanol/ammonia (s.g. 0.88) 6:1:1 v/v/v)
  4. customIsolation of the main band (RF 0.3) gave an oil which
  5. customcrystallized on trituration with acetone

Sources & evidence

ORD record
ord-eb7c5fa09e5d4b948d513a19dfe4453f
Source dataset
uspto-grants-1982_01
Patent number
US04309435

Reaction notes

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