Sodium Hydroxide → (2-Phenyl-1,3-oxazol-5-yl)methanamine

HRID 915669Notes

Reaction equation

HRID 915669 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH2:12][N:13]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>Cl>[C:1]1([C:7]2[O:8][C:9]([CH2:12][NH2:13])=[CH:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 691295772-(2-Phenyloxazol-5-ylmethyl)isoindole-1,3-dione

Product 1

HCID 57200720(2-Phenyl-1,3-oxazol-5-yl)methanamineYield 46.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Heat a suspension of 2-(2-phenyloxazol-5-ylmethyl)isoindole-1,3-dione (1.5 g, 4.94 mmol) in 6N HCl (75 mL) at reflux for 5 days. Cool, basify with 3 N sodium hydroxide, and extract with methylene chloride (2×150 mL). Dry the organic phase (Na2SO4), filter, and concentrate to afford 400 mg of the title compound as a yellow oil. MS: m/e=175 (MH+).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 5 days
  3. temperatureCool
  4. extractionextract with methylene chloride (2×150 mL)
  5. dry with materialDry the organic phase (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-a7c384468a744a3591e71dc1afc6c22b
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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