Water → HCID 66665541, compound

HRID 522429Notes

Reaction equation

HRID 522429 reaction equation
[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:17][C:18]([CH3:22])([CH3:21])[CH:19]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[C:18]([C:22]1[N:16]=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[C:2]2[C:3]=1[N:4]1[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]1)=[N:1]2)([CH3:21])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 12417PivalaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 17755357HCID 17755357, compound

Product 1

HCID 66665541HCID 66665541, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Preparation analogous to S. Sharma et al., J. Comb. Chem. 2007, 9, 783. A mixture of 20.9 g (100 mmol) of 2-imidazo[1,2-a]pyridin-2-ylphenylamine [127219-06-1], 42.1 g (500 mmol) of 2,2-dimethylpropanal [630-19-3] and 1.9 g (10 mmol) of p-toluenesulfonic acid hydrate in 500 ml of xylene is heated under reflux for 16 h, during which the water formed is removed by azeotropic distillation and a gentle stream of air is passed into the solution. After cooling, the solvent is removed in vacuo, the residue is taken up in 1000 ml of ethyl acetate, washed twice with 500 ml of water each time, once with 500 ml of saturated sodium chloride solution and dried over magnesium sulfate. After recrystallisation from ethanol twice, the solid is freed from low-boiling and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 180° C.). Yield: 9.1 g (33 mmol), 33%, purity: about 99.5% (NMR).

Workup

  1. customPreparation analogous to S
  2. temperatureis heated
  3. customformed
  4. customis removed by azeotropic distillation
  5. temperatureAfter cooling
  6. customthe solvent is removed in vacuo
  7. washwashed twice with 500 ml of water each time
  8. dry with materialonce with 500 ml of saturated sodium chloride solution and dried over magnesium sulfate
  9. customAfter recrystallisation from ethanol twice
  10. customby sublimation (p about 1×10−5 mbar, T about 180° C.)

Sources & evidence

ORD record
ord-dff45d941de94bbaa74ae8c3d3ba9df5
Source dataset
uspto-grants-2016_05
Patent number
US09331290B2

Reaction notes

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