Toluene → 5-Chloro-2-(4-chloromethylphenoxymethyl)imidazo[1,2-a]pyridine

HRID 2299727Notes

Reaction equation

HRID 2299727 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[N:11]2[CH:12]=[C:13]([CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([CH2:21]O)=[CH:19][CH:18]=3)[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1>O>[Cl:5][C:6]1[N:11]2[CH:12]=[C:13]([CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([CH2:21][Cl:3])=[CH:19][CH:18]=3)[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 22344568HCID 22344568, compound

Product 1

HCID 223445955-Chloro-2-(4-chloromethylphenoxymethyl)imidazo[1,2-a]pyridineYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (0.597 ml) was added dropwise to a mixture of 4-(5-chloroimidazo[1,2-a]pyridine-2-ylmethoxy)benzylalcohol (1.97 g), triethylamine (1.15 ml) and toluene (50 ml) at 0° C. After stirring for 1 hour, water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 5-chloro-2-(4-chloromethylphenoxymethyl)imidazo[1,2-a]pyridine (1.10 g, yield 52%) as colorless crystals. m.p. 114-115° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8c4a6141abfa4bc5a2327707b5a48d45
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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