Potassium Carbonate → (2-Isopropyl-4-methoxy-5-thiazol-4-yl-phenoxy)-acetonitrile

HRID 38399Notes

Reaction equation

HRID 38399 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]2[N:13]=[CH:14][S:15][CH:16]=2)=[CH:6][C:5]=1[OH:17])([CH3:3])[CH3:2].Br[CH2:19][C:20]#[N:21].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]2[N:13]=[CH:14][S:15][CH:16]=2)=[CH:6][C:5]=1[O:17][CH2:19][C:20]#[N:21])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 595986332-Isopropyl-4-methoxy-5-thiazol-4-yl-phenol

Product 1

HCID 59598608(2-Isopropyl-4-methoxy-5-thiazol-4-yl-phenoxy)-acetonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude 2-Isopropyl-4-methoxy-5-thiazol-4-yl-phenol from step 4 and bromoacetonitrile (0.33 g, 2.72 mmol) together with K2CO3 (0.94 g, 6.81 mmol) in anhydrous acetonitrile (30 ml) was heated at 60° C. for 3 hrs. The reaction mixture was partitioned between EtOAc and water. The combined organic extract was dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (10 to 20% EtOAc in Hexanes) gave (2-Isopropyl-4-methoxy-5-thiazol-4-yl-phenoxy)-acetonitrile (0.47 g, 72%) as an oil.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. extractionThe combined organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-144dbf6701b44a9c871e94b57c739f56
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

Loading…