Glycolic Acid → HCID 178423363, compound

HRID 1244317

Reaction equation

HRID 1244317 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10](O)(=O)[CH2:11]O.S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[ClH:17].[Cl:17][CH2:11][C:10]1[NH:1][C:2]2=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=[C:7]2[N:8]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 24386Thionyl ChlorideHCID 27344206-Methylpyridine-2,3-diamine

Product 1

HCID 178423363HCID 178423363, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.5 g 2,3-Diamino-6-methyl pyridine (4.0 mmol) and 0.37 g glycolic acid were heated at 150° C. for 1 h. The residue was suspended in chloroform (7.0 ml) treated with 1.5 ml thionyl chloride (20 mmol)for 4 h at reflux. The mixture was evaporated and the residue triturated with methanol. After concentration the residue was stirred over night in ether and the suspension was then filtered. The residue on the filter was dried to yield 0.67 g 2-chloromethyl-5-methyl-3H-imidazo[4,5-b]pyridine hydrochloride as a dark brown solid; M.p.: 225–230° C., (dec.).

Workup

  1. temperatureat reflux
  2. customThe mixture was evaporated
  3. customthe residue triturated with methanol
  4. concentrationAfter concentration the residue
  5. filtrationthe suspension was then filtered
  6. customThe residue on the filter was dried

Sources & evidence

ORD record
ord-30fdcfd2e2b948c78acfda84ab1152c8
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Linked notes

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