Water → HCID 15580723, compound

HRID 543814Notes

Reaction equation

HRID 543814 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:10]([CH3:11])[CH2:9][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)=[O:4].C(OC(=O)C)(=O)C.O>CN(C)C1C=CN=CC=1.ClCCl>[CH3:11][CH:10]1[CH2:9][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=[C:6]1[NH:5][C:3](=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 15580691HCID 15580691, compound

Product 1

HCID 15580723HCID 15580723, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 10.0 g. amount of 3-amino-4-methyl-1-phenyl-2-pyrazoline (prepared as described in Example 6) is dissolved in 50 ml. of acetic anhydride, then 500 mg. of 4-dimethylaminopyridine is added and the reaction mixture is allowed to stand at room temperature for 18 hours. The mixture is poured into water to separate a gum which solidifies and is collected by filtration. The solid is added with stirring to 150 ml. of methanol containing 10.0 g. of sodium hydroxide. After 30 minutes, the solvent is removed in vacuo and water is added to provide a gum which becomes solid. This solid is dissolved in dichloromethane, dried over anhydrous magnesium sulfate and passed through a short column of a hydrous magnesium silicate. The effluent is concentrated while adding hexane to yield crystals. The material is collected and dried to give 3.3 g. of the desired product as a white solid, m.p. 149°-150° C.

Workup

  1. customto separate a gum which
  2. filtrationis collected by filtration
  3. additionThe solid is added
  4. waitAfter 30 minutes
  5. customthe solvent is removed in vacuo and water
  6. additionis added
  7. customto provide a gum which
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe effluent is concentrated
  10. additionwhile adding hexane
  11. customto yield crystals
  12. customThe material is collected
  13. customdried
  14. customto give 3.3 g

Sources & evidence

ORD record
ord-44c15caad4704c40934e5ec64088b49a
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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