Potassium Carbonate → 5-Ethynyl-4-phenyl-thiazol-2-ylamine

HRID 1009046Notes

Reaction equation

HRID 1009046 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH2:18])[S:10][C:11]=2[C:12]#[C:13][Si](C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:12]([C:11]1[S:10][C:9]([NH2:18])=[N:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)#[CH:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866309584-Phenyl-5-trimethylsilanylethynyl-thiazol-2-ylamine

Product 1

HCID 866309595-Ethynyl-4-phenyl-thiazol-2-ylamineYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the above prepared 4-phenyl-5-trimethylsilanylethynyl-thiazol-2-ylamine (1.070 g, 3.927 mmol), dissolved in 14 mL of MeOH, was added K2CO3 (0.814 g, 1.5 eq.)) and the mixture was stirred for 2 h at ambient temperature. Pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with water and brine, drying over sodium sulfate, and evaporation to dryness, followed by flash chromatography (SiO2, hexane/ethyl acetate=7/3), gave 0.667 g of the title compound as dark brown viscous oil.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with ethyl acetate
  3. washwashing with water and brine
  4. dry with materialdrying over sodium sulfate, and evaporation to dryness

Sources & evidence

ORD record
ord-2f6099a8e59d40e6b754532988d4f3b6
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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