4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 19751072, compound

HRID 484223Notes

Reaction equation

HRID 484223 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][C:5]([N:11]=[C:12]2[N:20]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[S:13]2)=[C:4]([F:22])[CH:3]=1.[OH:23][CH2:24][CH2:25][C:26]1[S:30][CH:29]=[N:28][C:27]=1[CH3:31].C(N(CC)CC)C>C(OC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]([O:23][CH2:24][CH2:25][C:26]2[S:30][CH:29]=[N:28][C:27]=2[CH3:31])=[O:9])=[CH:6][C:5]([N:11]=[C:12]2[N:20]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[S:13]2)=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 8471TriethylamineHCID 19751066HCID 19751066, compound

Product 1

HCID 19751072HCID 19751072, compound

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent2×

Procedure

A solution of 3.6 g of 9-[4-chloro-2-fluoro-5-(chlorocarbonyl)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan7-one in 10 ml of methyl acetate is added dropwise, with stirring, at room temperature to a solution of 1.2 ml of 5-(2-hydroxyethyl)-4-methylthiazole and 1.5 ml of triethylamine in 50 ml of methyl acetate. After stirring at room temperature for 12 hours, the precipitated triethylamine hydrochloride is filtered off and the filtrate is concentrated by evaporation, yielding 3.8 g of the title compound in the form of an oil with nD22 1.6030.

Workup

  1. filtrationthe precipitated triethylamine hydrochloride is filtered off
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-cec8b37006a248808f77dd871427eb10
Source dataset
uspto-grants-1993_07
Patent number
US05229514

Reaction notes

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