Sodium Iodide → HCID 19698534, compound

HRID 862554Notes

Reaction equation

HRID 862554 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[CH2:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=1[NH:31][C:32](=[O:38])[O:33][CH2:34][CH2:35][O:36][CH3:37]>CC(C)=O>[CH3:37][O:36][CH2:35][CH2:34][O:33][C:32]([NH:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([CH3:30])[C:24]=1[CH2:23][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:38]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 21873989HCID 21873989, compoundHCID 538354172-Methoxyethyl 2-chloromethyl-3-methylphenylcarbamate

Product 1

HCID 19698534HCID 19698534, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g (11.41 mmol) of 8-amino-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde, 1.21 g (11.41 mmol) of anhydrous sodium carbonate, 0.17 g (1.14 mmol) of sodium iodide and 3.5 g (13.6 mmol) of 2-methoxyethyl 2-chloromethyl-3-methylphenylcarbamate in 30 ml of acetone is stirred at RT for 24 h and concentrated in a Rotavapor. The residue is treated with 100 ml of water and extracted with ethyl acetate, and the organic phase is dried with magnesium sulphate and concentrated in vacuo. The residue is recrystallized from toluene. 3.31 g (73%) of the title compound of m.p. 153°-155° C. are obtained.

Workup

  1. concentrationconcentrated in a Rotavapor
  2. additionThe residue is treated with 100 ml of water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried with magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-6ffeecee329f4fb5ab07bccd4fac3471
Source dataset
uspto-grants-1998_02
Patent number
US05719161

Reaction notes

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