Sodium Bicarbonate → HCID 23731082, compound

HRID 1354167Notes

Reaction equation

HRID 1354167 reaction equation
[I-].C[CH:3]=[N+:4]=[CH:5]C.[CH3:7][C:8]1[N:9]=[C:10]2[C:15]([OH:16])=[CH:14][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][N:11]2[C:22]=1[CH3:23].[C:24](=O)([O-])O.[Na+]>ClCCl>[CH3:7][C:8]1[N:9]=[C:10]2[C:15]([OH:16])=[C:14]([CH2:3][N:4]([CH3:5])[CH3:24])[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][N:11]2[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17954319HCID 17954319, compoundHCID 21892197N,N-dimethylmethyleneammoniumiodide

Product 1

HCID 23731082HCID 23731082, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Over a period of 30 minutes, N,N-dimethylmethyleneammonium iodide (Eschenmoser's salt, 435 mg, 2.35 mmol) is added to a solution of ethyl 2,3-dimethyl-8-hydroxy-imidazo[1,2-a]pyridine-6-carboxylate (500 mg, 2.14 mmol) in 15 ml of dichloromethane. The reaction mixture is stirred for 2.5 hours at ambient temperature and the formation of a colourless precipitate is observed. 20 ml portions of saturated sodium hydrogencarbonate solution and dichloromethane are added to the reaction mixture. The aqueous phase is extracted with dichloromethane (3×20 ml). The combined organic phases are washed with water (20 ml), dried over sodium sulfate, and evaporated to dryness. The title compound (578 mg, 93%) is isolated as a greenish foam containing traces of impurities.—1H NMR (CDCl3, 200 MHz): □=1.41 (t, 3 H), 2.40 (s, 12 H), 4.19 (s, 2 H), 4.37 (q, 2 H), 8.04 (s, 1 H).

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane (3×20 ml)
  2. washThe combined organic phases are washed with water (20 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-70efd975334548a2a3d19159daf46890
Source dataset
uspto-grants-2007_05
Patent number
US07223771B2

Reaction notes

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