Hydrochloric Acid → 4-(4-Methoxy-phenyl)-2-methyl-thiazole-5-carbonitrile

HRID 538590Notes

Reaction equation

HRID 538590 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[C:16]([Cu])#[N:17].Cl>N1C=CC=CC=1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:3]2[N:4]=[C:5]([CH3:7])[S:6][C:2]=2[C:16]#[N:17])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13764098HCID 13764098, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 666199524-(4-Methoxy-phenyl)-2-methyl-thiazole-5-carbonitrileYield 93.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-Bromo-4-(4-methoxy-phenyl)-2-methyl-thiazole (2.0 g, 7.0 mmol) in 15 ml of pyridine was added CuCN (3.10 g, 35.2 mmol) and the reaction mixture was heated to 150° C. in microwave for 2 h. After the completion of the reaction pH was adjusted to 3-4 with 1 N HCl solution and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (60-120 M, 12% EtOAc-Hexane) to get the desired product (1.5 g, 92%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified over silica gel (60-120 M, 12% EtOAc-Hexane)

Sources & evidence

ORD record
ord-cc238b8a019b41c49d0a88ca23831150
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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