Ethanol → N-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl]-N'-(4-methyl-2-thiazolyl)urea

HRID 851791Notes

Reaction equation

HRID 851791 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[N:9]=[CH:10][NH:11][C:12]=1[CH3:13].[H-].[Na+].[C:16]([NH:21][C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1)(OCC)=[O:17].C(O)C>N1C=CC=CC=1>[CH3:13][C:12]1[NH:11][CH:10]=[N:9][C:8]=1[CH2:7][S:6][CH2:5][CH2:4][NH:3][C:16]([NH:21][C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1)=[O:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 30159992-(((5-Methyl-1H-imidazol-4-yl)methyl)thio)ethylamine dihydrochlorideHCID 41623722-Carbethoxyamino-4-methylthiazole

Product 1

HCID 20501188N-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl]-N'-(4-methyl-2-thiazolyl)ureaYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3.40 g (13.9 mmole) of 4-[(2-aminoethyl)thiomethyl]-5-methylimidazole dihydrochloride stirred under flowing nitrogen in 100 ml of dry pyridine is added 1.27 g (ca. 27.9 mmole) of a 50 percent dispersion in oil of sodium hydride. After approximately 90 min. 24.3 g (13.1 mmole) of 2-carbethoxyamino-4-methylthiazole is added, and the resultant mixture is heated at reflux for 1 day. After cooling to room temperature, the mixture is filtered to remove insolubles, and the filtrate is concentrated at reduced pressure. The resultant gum is repeatedly dissolved in aqueous ethanol and dried in vacuo, triturated with pentane to remove mineral oil, and purified by column chromotography* on silica gel. Fractions containing the product are combined, partially concentrated, filtered and finally dried by concentration in vacuo, giving 2.40 g (7.2 mmole) of the desired product as an ethanol solvate. Structure assignment and solvation by one-half mole of ethanol per mole of product are supported by nmr.

Workup

  1. temperatureat reflux for 1 day
  2. filtrationthe mixture is filtered
  3. customto remove insolubles
  4. concentrationthe filtrate is concentrated at reduced pressure
  5. dissolutionThe resultant gum is repeatedly dissolved in aqueous ethanol
  6. customdried in vacuo
  7. customtriturated with pentane
  8. customto remove mineral oil
  9. custompurified by column chromotography* on silica gel
  10. additionFractions containing the product
  11. concentrationpartially concentrated
  12. filtrationfiltered
  13. customfinally dried by concentration in vacuo

Sources & evidence

ORD record
ord-c91ae1854f4245ccad471d683bbf9fb3
Source dataset
uspto-grants-1983_05
Patent number
US04386211

Reaction notes

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