Hydrochloric Acid → 2-(2-Isopropylthiopyrid-3-yloxy)-propionic acid methyl ester

HRID 55549

Reaction equation

HRID 55549 reaction equation
[CH3:1][O:2][C:3](=[O:7])[CH:4](Br)[CH3:5].[CH:8]([S:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:7])[CH:4]([O:18][C:17]1[C:12]([S:11][CH:8]([CH3:10])[CH3:9])=[N:13][CH:14]=[CH:15][CH:16]=1)[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 199579323-Pyridinol, 2-[(1-methylethyl)thio]-

Product 1

HCID 544930632-(2-Isopropylthiopyrid-3-yloxy)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

12.3 ml of 2-bromopropionic acid methyl ester are added dropwise at room temperature to a mixture of 16.9 g of 2-isopropylthio-3-hydroxypyridine and 15.2 g of potassium carbonate in 250 ml of dimethylformamide and the batch is stirred for 75 minutes. The suspension is introduced into a mixture of ice-water (300 ml), 50 ml of 2N hydrochloric acid and 300 ml of ethyl acetate, washed four times with 120 ml of water and 120 ml of ethyl acetate each time, and the organic phase is dried over sodium sulfate and concentrated by evaporation. 25.4 g of the desired intermediate are obtained in the form of a viscous oil.

Workup

  1. washwashed four times with 120 ml of water and 120 ml of ethyl acetate each time
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-cb746f3e77cc4c7ca2fa00427cf9c504
Source dataset
uspto-grants-1997_04
Patent number
US05625071

Linked notes

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