Water → HCID 12093263, compound

HRID 585271Notes

Reaction equation

HRID 585271 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O.[C-:26]#[N:27].[Na+].C(=O)(O)[O-].[K+].O>CS(C)=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:26]#[N:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 516893Potassium BicarbonateHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 12093263HCID 12093263, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)ethyl ester (5.00 g, 14.0 mmol), sodium cyanide (852 mg, 16.8 mmol), and potassium bicarbonate (1.70 g, 16.8 mmol) were combined and vigorously stirred in DMSO (50 mL) at 50° C. for 2 h, then overnight at 25° C. The mixture was then poured into H2O (50 mL) and extracted with Et2O (2×50 mL). The organic layer were combined then washed with H2O (50 mL), sat. NaCl (50 mL), dried over NaCl. The solvent was removed in vacuo to provide 2.90 g (98%) of product as a white powder: 1H NMR (400 MHz, CDCl3) δ 7.93 (m, 2H), 7.39 (m, 3H), 2.81 (t, 2H), 2.71 (t, 2H), 2.35 (s, 3H); MS (EI) 213.1 (M+H)+.

Workup

  1. customovernight
  2. customat 25° C
  3. extractionextracted with Et2O (2×50 mL)
  4. washThe organic layer were combined then washed with H2O (50 mL), sat. NaCl (50 mL)
  5. dry with materialdried over NaCl
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-096cb720772d41e48bc0852379c01cf0
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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