Urea → 5-(2-Methoxy-benzyl)-oxazol-2-ylamine

HRID 408481Notes

Reaction equation

HRID 408481 reaction equation
Cl[CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])[CH:3]=O.[NH2:14][C:15]([NH2:17])=[O:16].COC1C=CC=CC=1N>C(O)C>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][C:2]1[O:16][C:15]([NH2:17])=[N:14][CH:3]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 70002-MethoxyanilineHCID 57464352HCID 57464352, compound

Product 1

HCID 600275125-(2-Methoxy-benzyl)-oxazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-(2-methoxylphenyl)-propionaldehyde (10 g, crude from above) and urea (9.6 g, 0.16 mol) was dissolved in ethanol (250 mL) and then heated to reflux overnight. The solvent was evaporated to dryness. The residue was diluted with dichloromethane (250 mL) and then washed with sodium hydroxide (10% aqueous solution, 100 mL) and water (50 mL). The organic layer was extracted three times with hydrochloric acid (5% aqueous solution, 250 mL). The combined aqueous layers were adjusted to pH 9 to 10 with a 10% aqueous solution of sodium hydroxide and then extracted three times with dichloromethane (300 mL). The organic layer was separated, dried over sodium sulfate, and evaporated to dryness. The crude product was purified by silica gel column chromatography to yield the yellow-red solid product. (0.72 g, 0.35% from 2-methoxyaniline). ESI-MS m/z calc. 204.1. found; 205.1 (M+1)+ 1H NMR (CDCl3) δ 7.26-7.20 (m, 1H), 7.14 (d, J=7.2 Hz, 1H), 6.91-6.86 (m, 2H), 6.35 (s, 1H), 4.49 (bs, 2H), 3.85 (s, 2H), 3.82 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated to dryness
  4. additionThe residue was diluted with dichloromethane (250 mL)
  5. washwashed with sodium hydroxide (10% aqueous solution, 100 mL) and water (50 mL)
  6. extractionThe organic layer was extracted three times with hydrochloric acid (5% aqueous solution, 250 mL)
  7. extractionextracted three times with dichloromethane (300 mL)
  8. customThe organic layer was separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness
  11. customThe crude product was purified by silica gel column chromatography
  12. customto yield the yellow-red solid product

Sources & evidence

ORD record
ord-b1a3ad7e085942f6827cb8339845ad29
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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