4-Methylbenzenethiol → HCID 21162553, compound

HRID 894239Notes

Reaction equation

HRID 894239 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.Br[C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1>CN(C)C=O>[CH3:8][C:1]1[CH:6]=[CH:5][C:4]([S:7][C:10]2[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 78114-MethylbenzenethiolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162553HCID 21162553, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Using reagent quantities identical to that of Example 9, p-toluenethiol and cuprous oxide were combined in 45 ml. of dimethylformamide heated at 135° C. for about 1.5 hours, cooled somewhat, 5-bromofuran-3-carboxylic acid in 40 ml. of dimethylformamide added, and the mixture refluxed for 24 hours. Crude product (185 mg.) was recovered according to the procedure of Example 10. Recrystallization from methanol/water afforded purified 5-(4-methylphenylthio)furan-3-carboxylic acid (135 mg., m.p. 116°-119° C.).

Workup

  1. temperaturecooled somewhat
  2. temperaturethe mixture refluxed for 24 hours
  3. customCrude product (185 mg.) was recovered
  4. customRecrystallization from methanol/water
  5. customafforded
  6. custompurified 5-(4-methylphenylthio)furan-3-carboxylic acid (135 mg., m.p. 116°-119° C.)

Sources & evidence

ORD record
ord-ee18a6322566450e8af0210a92b334c3
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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