1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 20237850, compound

HRID 365216Notes

Reaction equation

HRID 365216 reaction equation
[NH2:1][C:2]1[C:3]([CH3:14])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[CH3:7].Br[CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:14][C:3]1[C:2]([NH:1][CH2:16][CH2:17][N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])=[C:6]([CH3:7])[N:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:4]=1

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 70370103,5-dimethyl-1-phenyl-1H-pyrazol-4-amine

Product 1

HCID 20237850HCID 20237850, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 38.1 g. 4-amino-3,5-dimethyl-1-phenylpyrazole, 77.5 g. N-(2-bromoethyl)-phthalimide and 42 g. potassium carbonate in 600 ml. acetonitrile is boiled for 15 hours, with stirring. After cooling, insoluble material is filtered off with suction and the filtrate is evaporated. The residue is stirred with methylene chloride and suction filtered and the filtrate is purified on a silica gel column using, as elution agents, first methylene chloride and then methylene chloride-ethyl acetate (6:4 v/v). There are obtained 41 g. (56% of theory) of a brownish oil.

Workup

  1. additionA mixture of 38.1 g
  2. temperatureAfter cooling
  3. filtrationinsoluble material is filtered off with suction
  4. customthe filtrate is evaporated
  5. stirringThe residue is stirred with methylene chloride and suction
  6. filtrationfiltered
  7. customthe filtrate is purified on a silica gel column
  8. washusing, as elution agents, first methylene chloride
  9. customThere are obtained 41 g

Sources & evidence

ORD record
ord-ef007c90b7324337b3ba01f26b5ce491
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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