Potassium Iodide → 4-Tert-butyl-2-(2,4-diformylphenoxymethyl)thiazole

HRID 487672Notes

Reaction equation

Br[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[N:7]=1.[CH:12]([C:14]1[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([CH:21]=1)[CH:19]=[O:20])=[O:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:8]([C:6]1[N:7]=[C:3]([CH2:2][O:22][C:17]2[CH:16]=[CH:15][C:14]([CH:12]=[O:13])=[CH:21][C:18]=2[CH:19]=[O:20])[S:4][CH:5]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-bromomethyl-4-tert-butylthiazole (1.05 g), 5-formyl-2-hydroxybenzaldehyde (0.74 g), potassium carbonate (0.89 g) and potassium iodide (small mass) in N,N-dimethylformamide was stirred at 50° C. for 5 hours. After being cooled, the resulting solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-(2,4-diformylphenoxymethyl)thiazole (1.0 g).

Workup

temperatureAfter being cooled
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a syrup
washeluted with a mixture of toluene and ethyl acetate
additionThe fractions containing object compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5a3bfa456f6442678f9e09506ade3b88
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05296495

Reaction notes

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