4-Chlorobenzoyl chloride → HCID 20335981, compound

HRID 1706396Notes

Reaction equation

HRID 1706396 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][N:3]1[CH3:14].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C(Cl)(Cl)Cl>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]2[CH2:6][N:2]([CH3:1])[N:3]([CH3:14])[CH2:4]2)=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 20335988HCID 20335988, compound

Product 1

HCID 20335981HCID 20335981, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 10 g. (0.0525 mole) of 1,2-dimethyl-4-anilinopyrazolidine in 50 ml. of chloroform was added with stirring 9.15 g. (0.0525 mole) of p-chlorobenzoyl chloride with the temperature not exceeding 50° C. On completion of addition the solution was refluxed for one hour, cooled to room temperature and extracted with dilute sodium hydroxide. The chloroform layer was dried over sodium sulfate and concentrated at reduced pressure to give an oil which crystallized upon cooling. The solid was recrystallized twice from ligroin. Yield 13.1 g. (76%); m.p. 104°-108° C.

Workup

  1. customexceeding 50° C
  2. additionOn completion of addition the solution
  3. temperaturewas refluxed for one hour
  4. extractionextracted with dilute sodium hydroxide
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto give an oil which
  8. customcrystallized
  9. temperatureupon cooling
  10. customThe solid was recrystallized twice from ligroin

Sources & evidence

ORD record
ord-bb6cc2c34c2d4b5ca6713045e78d8c76
Source dataset
uspto-grants-1980_06
Patent number
US04207327

Reaction notes

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