4-Hydroxybenzaldehyde → HCID 10423882, compound

HRID 2382589Notes

Reaction equation

HRID 2382589 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].COS(=O)O[CH2:16][CH2:17][NH:18][C:19]1[O:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1>CN(C=O)C>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[NH:18][CH2:17][CH2:16][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 86654535HCID 86654535, compound2×

Product 1

HCID 10423882HCID 10423882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 4-hydroxybenzaldehyde (6.1 g, 50 mmol) in dry DMF (40 mL), was added sodium hydride (2.2 g, 55 mmol, 60% suspension) under stirring, in a nitrogen atmosphere at room temperature. The thick solution was diluted with dry DMF (20 mL). Sulfurous acid 2-(benzooxazol-2-ylamino)-ethyl ester methyl ester [compound of Step III] (14 g, 55 mmol) dissolved in dry DMF was added dropwise to the reaction mixture over a period of 20 min and the resulting mixture was heated to 80° C. for 1 hour. The reaction mixture was poured on crushed ice and then extracted with ethyl acetate (3×200 mL). The ethyl acetate layer was washed with water and brine, dried over anhydrous sodium sulfate, concentrated and purified using silica gel column and 50% ethyl acetate in petroleum ether to give 4-[2-(benzooxazol-2-ylamino)-ethoxy]-benzaldehyde.

Workup

  1. additionwas added dropwise to the reaction mixture over a period of 20 min
  2. temperaturethe resulting mixture was heated to 80° C. for 1 hour
  3. additionThe reaction mixture was poured
  4. customon crushed ice
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. washThe ethyl acetate layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-3531196f309e4f4a81f037c3eab18c41
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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