Benzene → 5-(p-Chlorophenyl)-2-furoic Acid 2,2-Dimethylhydrazide

HRID 236271

Reaction equation

HRID 236271 reaction equation
C[NH:2][NH:3][CH3:4].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17](Cl)=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[CH:20]1C=CC=CC=1>>[CH3:20][N:3]([CH3:4])[NH:2][C:17]([C:15]1[O:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)=[O:18]

Participants

4

Reactant 3

HCID 241BenzeneHCID 13221,2-DimethylhydrazineHCID 27719705-(4-chlorophenyl)furan-2-carbonyl Chloride

Product 1

HCID 137704455-(p-Chlorophenyl)-2-furoic Acid 2,2-Dimethylhydrazide

Procedure

To a solution of 36 g (0.60 mole) of dimethylhydrazine and 150 ml of benzene was added portionwise 60 g (0.25 mole) of 5-(p-chlorophenyl)-2-furoyl chloride with the temperature being controlled below 50° by means of an ice bath. The reaction mixture was refluxed for 2 hours with dissolution, cooled and the resulting precipitate filtered, washed with water and dried at 60° to yield 48 g (73%). An analytical sample was prepared by recrystallizing a sample from ethyl acetate/Darco and drying in the vacuum pistol at room temperature, m.p. 150°-152°.

Workup

  1. custombeing controlled below 50° by means of an ice bath
  2. temperatureThe reaction mixture was refluxed for 2 hours with dissolution
  3. temperaturecooled
  4. filtrationthe resulting precipitate filtered
  5. washwashed with water
  6. customdried at 60°
  7. customto yield 48 g (73%)
  8. customAn analytical sample was prepared
  9. customby recrystallizing a sample from ethyl acetate/Darco
  10. customdrying in the vacuum pistol at room temperature

Sources & evidence

ORD record
ord-4cade93daca94577a57860487b344943
Source dataset
uspto-grants-1987_02
Patent number
US04643996

Linked notes

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