Sulfuric Acid → Thiazole, 4,5-bis(4-methoxyphenyl)-2-(4-fluorophenyl)-

HRID 2059206Notes

Reaction equation

HRID 2059206 reaction equation
S(=O)(=O)(O)O.[C:6]1([C:14]([CH:16]([C:18]2[CH:25]=[CH:24][C:21]([O:22][CH3:23])=[CH:20][CH:19]=2)O)=O)[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[CH:8][CH:7]=1.[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[S:32])=[CH:29][CH:28]=1>O1CCOCC1>[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]2[S:32][C:16]([C:18]3[CH:25]=[CH:24][C:21]([O:22][CH3:23])=[CH:20][CH:19]=3)=[C:14]([C:6]3[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[CH:8][CH:7]=3)[N:33]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 954154,4'-DimethoxybenzoinHCID 7372234-Fluorothiobenzamide

Product 1

HCID 3062249Thiazole, 4,5-bis(4-methoxyphenyl)-2-(4-fluorophenyl)-Yield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Three ml. of concentrated sulfuric acid, 250 ml. of dioxane, 27.2 g. (0.10 mole) of anisoin, and 15.5 g. (0.10 mole) of 4-fluorothiobenzamide were placed in a round bottom flask. The mixture was stirred at reflux for 3 days, then cooled to room temperature, and poured onto ice. Then the mixture was extracted with ethyl acetate, washed with water, and dried over sodium sulfate. After the ethyl acetate was evaporated, a crude solid of 35 g. remained. The solid was then recrystallized from ethyl acetate and weighed 27.5 g. (70% yield). It had a melting point of about 140°-141.5° C. and the mass spectrum showed the expected molecular ion at m/e=391.

Workup

  1. temperatureat reflux for 3 days
  2. additionpoured onto ice
  3. extractionThen the mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customAfter the ethyl acetate was evaporated
  7. customThe solid was then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b5160310e3b04927b12bb2da7820c530
Source dataset
uspto-grants-1982_03
Patent number
US04322428

Reaction notes

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