Potassium Carbonate → HCID 13135252, compound

HRID 1632673Notes

Reaction equation

HRID 1632673 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CS([C:26]1[S:27][C:28]2[C:33]([N:34]=1)=[CH:32][CH:31]=[C:30]([Cl:35])[N:29]=2)(=O)=O>C(#N)C>[Cl:35][C:30]1[N:29]=[C:28]2[S:27][C:26]([O:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:14][CH:15]=3)=[N:34][C:33]2=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterHCID 13135251HCID 13135251, compound

Product 1

HCID 13135252HCID 13135252, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

21 g (0.1 mole) of ethyl 2-(4'-hydroxyphenoxy)propionate were heated under reflux for 1 hour with 16.6 g (0.12 mole) of potassium carbonate in 250 ml of acetonitrile in order to form the salt. After adding 24.9 g (0.1 mole) of 2-methylsulfonyl-5-chlorothiazolo[5,4-b]pyridine, the reaction mixture was heated under reflux for a further 10 hours. The salt constituent was filtered off while hot and the solvent was removed. The residue was distilled in a high vacuum. This gave 33.6 g (89% of theory) of ethyl 2-[4-(5-chlorothiazolo[5,4-b]pyridin-2-yloxy)-phenoxy]-propionate, of boiling point 204°-207° C./0.01 mbar, which crystallized completely after a little time (melting point 60°-62° C.). ##STR13##

Workup

  1. customto form the salt
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for a further 10 hours
  4. filtrationThe salt constituent was filtered off while hot and the solvent
  5. customwas removed
  6. distillationThe residue was distilled in a high vacuum
  7. customThis gave 33.6 g (89% of theory) of ethyl 2-[4-(5-chlorothiazolo[5,4-b]pyridin-2-yloxy)-phenoxy]-propionate, of boiling point 204°-207° C./0.01 mbar, which crystallized completely after a little time (melting point 60°-62° C.)

Sources & evidence

ORD record
ord-124a3874aa72408cb4eecdb4106904a1
Source dataset
uspto-grants-1984_10
Patent number
US04477276

Reaction notes

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