Water → HCID 135431815, compound

HRID 1247225Notes

Reaction equation

HRID 1247225 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[N:8][C:7]=2[CH:6]=[C:5]([OH:19])[CH:4]=1.C1OCCOCCOCCOCCOCCOC1.[C-:38]#[N:39].[K+].O>CN(C)C=O>[OH:19][C:5]1[CH:4]=[C:3]([CH2:2][C:38]#[N:39])[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[N:8][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 135483639HCID 135483639, compound

Product 1

HCID 135431815HCID 135431815, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(bromomethyl)-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol (122 mg, 0.40 mmol) in N,N-dimethylformamide (1.5 mL) was added 18-crown-6-ether (202 mg, 0.80 mmol) and potassium cyanide (131 mg, 2 mmol). The reaction mixture was allowed to stir for 2 h and then poured into water and extracted with EtOAc. The organic extracts were washed with brine and dried over MgSO4. Evaporation and flash chromatography (50%–60% EtOAc/petroleum ether) gave (80 mg, 75% yield) of the product as a gray solid, m.p. 170–180° C.; MS m/e 265 (M−H)+. Analysis for C15H10N2O3×1.5H2O.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customEvaporation and flash chromatography (50%–60% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-4a95d05f4496463aa74618255c57f432
Source dataset
uspto-grants-2006_10
Patent number
US07129258B2

Reaction notes

Loading…