Chlorosuccinimide → 3,5-Dichloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine

HRID 2171538Notes

Reaction equation

HRID 2171538 reaction equation
[Cl:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.[Cl:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[Cl:19][C:8]1[N:7]2[C:2]([Cl:1])=[N:3][C:4]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[CH:5][C:6]2=[N:10][CH:9]=1

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 59312932HCID 59312932, compound

Product 1

HCID 593129023,5-Dichloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg (1.0 mmol) of 5-chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) are suspended in chloroform (15 ml), 240 mg (1.8 mmol) of N-chlorosuccinimide are added, and the reaction mixture is stirred at RT for 12 h. The reaction mixture is diluted with ethyl acetate (100 ml) and water (75 ml), and the organic phase is separated off, dried over magnesium sulphate and concentrated in a rotary evaporator. The residue is stirred with diethyl ether (20 ml), and the solid is filtered off with suction and dried. 63 mg (18% of theory) of the product are isolated.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in a rotary evaporator
  4. stirringThe residue is stirred with diethyl ether (20 ml)
  5. filtrationthe solid is filtered off with suction
  6. customdried
  7. custom63 mg (18% of theory) of the product are isolated

Sources & evidence

ORD record
ord-bcbf8ff6dbe842a0a34b7f00872751fc
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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