Pyridine → HCID 20187066, compound

HRID 2308572Notes

Reaction equation

HRID 2308572 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:15][CH:16]([CH2:20][Cl:21])[C:17](Cl)=[O:18]>C(Cl)(Cl)Cl>[Cl:15][CH:16]([CH2:20][Cl:21])[C:17]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 78124-ChloroanilineHCID 111020Propanoyl chloride, 2,3-dichloro-

Product 1

HCID 20187066HCID 20187066, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 12.8 grams (0.10 mole) of 4-chloroaniline in 85 ml of chloroform was added 8 ml of pyridine. The mixture was cooled to 10° and 16.1 grams (0.10 mole) of 2,3-dichloropropionyl chloride was added dropwise at such a rate that the reaction mixture temperature did not exceed 35°. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under reduced pressure to a solid residue. The solid was slurried with water and collected by filtration. The dried solid was recrystallized from methylcyclohexane-ethyl acetate using silica gel as a decolorant to give 19.7 grams of 2,3-dichloro-N-(4-chlorophenyl)propanamide; mp 127.5°-129°.

Workup

  1. temperatureThe mixture was cooled to 10°
  2. customdid not exceed 35°
  3. additionUpon completion of addition
  4. concentrationThe reaction mixture was concentrated under reduced pressure to a solid residue
  5. filtrationcollected by filtration
  6. customThe dried solid was recrystallized from methylcyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-80907fb281514df1ad417a9fe3c84412
Source dataset
uspto-grants-1987_09
Patent number
USH0000327

Reaction notes

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