Water → HCID 10569271, compound

HRID 1290169Notes

Reaction equation

HRID 1290169 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:12]=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[Cl:21]N1C(=O)CCC1=O.O>C(O)C>[Cl:21][C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]3[C:16]([Cl:20])=[CH:17][CH:18]=[CH:19][C:2]=3[Cl:1])[C:7]2=[N:14][C:13]=1[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 10852230HCID 10852230, compound

Product 1

HCID 10569271HCID 10569271, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8-(2,6-dichlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (100 mg) in ethanol (2 ml) was added in one portion N-chlorosuccinimide (65.3 mg) at ambient temperature. After stirring for 1 hour at the same temperature, water was added thereto, and the mixture was extracted with methylene chloride. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was subjected to a column chromatography on silica gel eluting with 1% solution of methanol in methylene chloride. The desired residue was recrystallized with a mixture of benzene and n-hexane to give 3-chloro-8-(2,6-dichlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (63 mg).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe desired residue was recrystallized with a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-862de29ae2be4025843d1777f9b58efd
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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