Acetic Anhydride → HCID 15580724, compound

HRID 543812Notes

Reaction equation

HRID 543812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH3:13])[C:10]([NH:14][CH:15]=[O:16])=[N:9]2)=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH:11]([CH3:13])[C:10]([NH:14][C:15](=[O:16])[CH3:17])=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 15580714HCID 15580714, compound

Product 1

HCID 15580724HCID 15580724, compound

Procedure

A 9.0 g. amount of 3-amino-1-(p-chlorophenyl)-4-methyl-2-pyrazoline (prepared as described in Example 23) is dissolved in 54.0 ml. of acetic anhydride. The warm solution is allowed to stand for 16 hours at room temperature with some solid separation. The solid is collected by filtration and is dissolved in methanol. Then 1 N potassium hydroxide in methanol is added to make basic. After 15 minutes at room temperature, the solvent is removed in vacuo and water is added to separate a solid. The solid is collected and recrystallized from dichloromethane-hexane to give 6.5 g. of the desired product as white crystals, m.p. 172°-173° C.

Workup

  1. customto stand for 16 hours at room temperature with some solid separation
  2. filtrationThe solid is collected by filtration
  3. dissolutionis dissolved in methanol
  4. additionThen 1 N potassium hydroxide in methanol is added
  5. customthe solvent is removed in vacuo and water
  6. additionis added
  7. customto separate a solid
  8. customThe solid is collected
  9. customrecrystallized from dichloromethane-hexane
  10. customto give 6.5 g

Sources & evidence

ORD record
ord-aae2abd47c6747e395b54bf9e68b78d9
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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