m-Chloroperbenzoic acid → HCID 66854770, compound

HRID 1530007Notes

Reaction equation

HRID 1530007 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[S:10][C:11]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(#N)C>[O-:31][N+:20]1[CH:19]=[CH:18][C:17]([C:9]2[S:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 44384908HCID 44384908, compound

Product 1

HCID 66854770HCID 66854770, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of ethyl 4-phenyl-2-pyridin-4-yl-1,3-thiazole-5-carboxylate (2.6 g, 8.5 mmol) produced in the above in acetonitrile (300 mL) was added m-chloroperbenzoic acid (containing water, about 70%, 3.9 g, about 16.0 mmol), and the mixture was stirred at room temperature for 2 days. The reaction solution was concentrated under reduced pressure to about 100 mL, and the obtained suspension was diluted with ethyl acetate (300 mL), and washed successively with saturated aqueous sodium bisulfite solution (150 mL×2) and saturated aqueous sodium carbonate solution (150 mL×2). The combined aqueous layer was extracted with ethyl acetate (200 mL×2). The combined organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained solid was washed with ethyl acetate, and collected by filtration to give the title compound (2.0 g, 72%) as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure to about 100 mL
  2. additionthe obtained suspension was diluted with ethyl acetate (300 mL)
  3. washwashed successively with saturated aqueous sodium bisulfite solution (150 mL×2) and saturated aqueous sodium carbonate solution (150 mL×2)
  4. extractionThe combined aqueous layer was extracted with ethyl acetate (200 mL×2)
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. filtrationthe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained solid was washed with ethyl acetate
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ea54d772cd55422c899156e09cbd37e1
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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