Ethanol → HCID 178431969, compound

HRID 851790Notes

Reaction equation

HRID 851790 reaction equation
Cl.Cl.[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH2:16])[N:11]=1)[C:4]([NH2:6])=N.[H-].[Na+].[C:19]([NH:24][C:25]1[S:26][CH:27]=[C:28]([CH3:30])[N:29]=1)(OCC)=[O:20].C(O)C.[N:34]1C=CC=CC=1>>[NH2:34][N:6]=[CH:4][NH:3][C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH:16][C:19]([NH:24][C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[O:20])[N:11]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 1049PyridineHCID 24758Sodium hydrideHCID 41623722-Carbethoxyamino-4-methylthiazoleHCID 178478806HCID 178478806, compound

Product 1

HCID 178431969HCID 178431969, compound

Procedure

To 4.60 g (15.1 mmole) of 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole dihydrochloride stirred under flowing nitrogen in 170 ml of dry pyridine is added 1.38 g (ca. 30.3 mmole) of a 50 percent dispersion in oil of sodium hydride. After about 1 hour 2.80 g (15.0 mmole) of 2-carbethoxyamino-4-methylthiazole is added, and the resultant mixture is heated at reflux for 2 days. After partial cooling, the mixture is decanted through a sintered glass funnel using suction, all residues being discarded, and the filtered supernatant is concentrated in vacuo to a thick gum. Residual mineral oil is removed by trituration with several portions of diethyl ether and pentane, and the residue is purified by column chromatography* on silica gel. Fractions containing the product are combined, partially concentrated, filtered, and thoroughly dried by concentration in vacuo, giving 1.20 g (3.1 mmole) of the desired product as an ethanol solvate. Structure assignment and solvation by one quarter mole of ethanol per mole of product are supported by nmr.

Workup

  1. temperatureat reflux for 2 days
  2. customAfter partial cooling, the mixture is decanted through a sintered glass funnel
  3. concentrationthe filtered supernatant is concentrated in vacuo to a thick gum
  4. customResidual mineral oil is removed by trituration with several portions of diethyl ether and pentane
  5. customthe residue is purified by column chromatography* on silica gel
  6. additionFractions containing the product
  7. concentrationpartially concentrated
  8. filtrationfiltered
  9. customthoroughly dried by concentration in vacuo

Sources & evidence

ORD record
ord-242d30d0afa24a6c88742b61b36d86aa
Source dataset
uspto-grants-1983_05
Patent number
US04386211

Reaction notes

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