Chlorosuccinimide → HCID 20508949, compound

HRID 1758800Notes

Reaction equation

HRID 1758800 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[CH:13]=[N:14][CH:15]=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1.[Cl:16]N1C(=O)CCC1=O>ClCCl>[Cl:16][C:15]1[N:14]=[CH:13][N:12]2[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:8][CH:9]=[N:10][C:11]=12

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20508955HCID 20508955, compound

Product 1

HCID 20508949HCID 20508949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.01 mol of 4-(3-pyridyl)imidazo[1,5-a]pyrimidine (prepared as described in Example 24) and N-chlorosuccinimide (0.013 mol) in 50 ml. of dichloromethane can be refluxed on a steam bath for 3 hours. The reaction mixture can be poured into 100 ml. of ice cold 2.5 N sodium hydroxide solution, the organic layer separated, and dried over anhydrous sodium sulfate, and then passed through a short column of hydrous magnesium silicate. The effluent can be refluxed on a steam bath with the gradual addition of n-hexane until crystallization occurs. The mixture can be cooled and the desired product collected by filtration to produce 8-chloro-4-(3-pyridyl)imidazo[1,5-a]pyrimidine.

Workup

  1. additionThe reaction mixture can be poured into 100 ml
  2. customof ice cold 2.5 N sodium hydroxide solution, the organic layer separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. temperatureThe effluent can be refluxed on a steam bath with the gradual addition of n-hexane until crystallization
  5. temperatureThe mixture can be cooled
  6. filtrationthe desired product collected by filtration

Sources & evidence

ORD record
ord-14bbd988e578452786796909fe56a5e8
Source dataset
uspto-grants-1983_02
Patent number
US04374988

Reaction notes

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