Water → HCID 22625603, compound

HRID 1600553Notes

Reaction equation

HRID 1600553 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH:17]=1.[Cl:18]N1C(=O)CCC1=O.O.CCCCCC.C(OCC)(=O)C>CN(C)C=O>[Cl:18][C:17]1[N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:11]2=[N:10][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 21226206Ethyl acetate hexane2×HCID 22625614HCID 22625614, compound

Product 1

HCID 22625603HCID 22625603, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.0 g (3.7 mmol) of 2-(2,4-dichlorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine and 0.6 g (4.5 mmol) of N-chlorosuccinimide was stirred in 15 ml of dimethylformamide at room temperature overnight followed by heating at 70° C. for 20 minutes. An excess of water was added and the aqueous mixture extracted with 200 ml of ethyl acetate. The separated organic layer layer was washed with water, saturated aqueous sodium bicarbonate, and brine. After drying over magnesium sulfate, the solvent was removed in vacuo to give a oily residue. Silica gel column chromatography (3:1 followed by 1:1 hexane/ethyl acetate followed in turn by 2:1 ethyl acetate/hexane) afforded the title compound as the main component (0.65 g, m.p. 99-101° C.).

Workup

  1. extractionthe aqueous mixture extracted with 200 ml of ethyl acetate
  2. washThe separated organic layer layer was washed with water, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give a oily residue

Sources & evidence

ORD record
ord-f84971f69f6747a09382d8989b481871
Source dataset
uspto-grants-1999_11
Patent number
US05977028

Reaction notes

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