Ethanol → 4-(4-Methylphenyl)thiazole

HRID 1378574Notes

Reaction equation

HRID 1378574 reaction equation
ClC1C=CC=CC=1[C:8]1[S:9][C:10](C2C=CC(SC)=CC=2)=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:12]=1.C(O)C.OOS([O-])=O.[K+]>O>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:12]=[CH:8][S:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 23707502Potassium hydroxy sulfiteHCID 537138882-(2-Chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole

Product 1

HCID 44049994-(4-Methylphenyl)thiazoleYield 225.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL one-neck round-bottom flask, equipped with provisions for magnetic stirring, was charged with 2-(2-chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole from Step 4 (0.243 g, 0.596 mmol) and aqueous ethanol (25 mL). Oxone®(1.10 g, 1.787 mmol) was added, and the suspension was stirred at room temperature for 16 hours. Water (25 mL) was added, and the product precipitated. The suspension was cooled to 0° C. and held for one hour. The product was filtered, washed with water (25 mL), and dried to yield 2-(2-chlorophenyl)-5-methylsulfonylphenyl)-4-(4-methylphenyl)thiazole (0.236 g, 90%) as a white solid: mp 185°-187 ° C. 1H NMR (CDCl3) 300 MHz 8.40(m, 1H), 7.89(d, J=8.26 Hz, 2H), 7.61 (d, J=8.46 Hz, 2H), 7.54-7.37 (m, 5H), 7.16 (d, J=7.85 Hz, 2H), 3.09(s, 3H), 2.38(s, 3H). Mass spectrum: MH+ =439.

Workup

  1. customA 100 mL one-neck round-bottom flask, equipped with provisions for magnetic stirring
  2. customthe product precipitated
  3. temperatureThe suspension was cooled to 0° C.
  4. waitheld for one hour
  5. filtrationThe product was filtered
  6. washwashed with water (25 mL)
  7. customdried

Sources & evidence

ORD record
ord-8145c8a894e94494a4e9b7521f5fafe4
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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