3,5-Dimethylaniline → HCID 21162434, compound

HRID 894241Notes

Reaction equation

HRID 894241 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.CC1C=C(C=C(C)C=1)N.Br[C:20]1[O:24][CH:23]=[C:22]([C:25]([OH:27])=[O:26])[CH:21]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:20]2[O:24][CH:23]=[C:22]([C:25]([OH:27])=[O:26])[CH:21]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 79493,5-DimethylanilineHCID 1175483,5-DimethylbenzenethiolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162434HCID 21162434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3,5-Dimethylthiophenol (4.33 g., 31.4 mmoles; prepared from 3,5-dimethylaniline by the procedures of Tarbell and Fukushima, Org. Synth. III, 809) and cuprous oxide (2.25 g., 15.7 mmoles) were reacted in 40 ml. of dimethylformamide at 140° C. for three hours. The mixture was cooled slightly and 5-bromofuran-3-carboxylic acid (3.0 g., 15.7 mmoles) in 40 ml. of dimethylformamide added. The mixture was refluxed for approximately 16 hours. Isolation of crude product as an oil was according to the procedure of Example 16 below. The oil was chromatographed on silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant. Product was recovered by evaporation of clean, middle fractions and trituration with water (706 mg.). Recrystallization from methanol/water gave purified 5-(3,5-dimethylphenylthio)furan-3-carboxylic acid (440 mg., m.p. 82°-86° C., m/e 248).

Workup

  1. temperatureThe mixture was cooled slightly
  2. temperatureThe mixture was refluxed for approximately 16 hours
  3. customThe oil was chromatographed on silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant
  4. customProduct was recovered by evaporation of clean, middle fractions and trituration with water (706 mg.)
  5. customRecrystallization from methanol/water
  6. customgave
  7. custompurified 5-(3,5-dimethylphenylthio)furan-3-carboxylic acid (440 mg., m.p. 82°-86° C., m/e 248)

Sources & evidence

ORD record
ord-ba8844710eb347ec96de13e390098505
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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