Water → 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanal O-(phenylcarbamoyl)oxime

HRID 42711Notes

Reaction equation

HRID 42711 reaction equation
[OH2:1].[C:2]1([C:8]2[N:9]=[C:10]([CH2:19][CH2:20]C=O)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:32](#[N:34])C>C(N(CC)CC)C>[C:23]1([NH:29][C:30]([O:1][N:34]=[CH:32][CH2:20][CH2:19][C:10]2[O:11][C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:9]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342Acetonitrile2×HCID 7672Phenyl isocyanateHCID 133100023-(4,5-Diphenyl-1,3-oxazol-2-yl)propanal

Product 1

HCID 768004173-(4,5-Diphenyl-1,3-oxazol-2-yl)propanal O-(phenylcarbamoyl)oxime

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

To a cooled (ice and water bath) and stirred solution of 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanal (300 mg, 1.02 mmol, Pridgen L. N. et al in Tetrahedron Lett., 25(27), 2835 (1984)) in dry acetonitrile (10 ml), 2-3 drops of triethylamine was added. A solution of phenyl isocyanate in 2 ml of dry acetonitrile was added dropwise at such rate, that the internal temperature remained below 30° C. The resulting reaction mixture was stirred at room temperature until the starting material was consumed (19 h, monitored by TLC). The light precipitate was filtered off and the solvent was evaporated in vacuo. The yellow oily crude product was purified by column chromatography with dichloromethane as eluent and crystallized from n-hexane.

Workup

  1. additionwas added
  2. customremained below 30° C
  3. customThe resulting reaction mixture
  4. customwas consumed (19 h, monitored by TLC)
  5. filtrationThe light precipitate was filtered off
  6. customthe solvent was evaporated in vacuo
  7. customThe yellow oily crude product was purified by column chromatography with dichloromethane as eluent
  8. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-7adb683f7edb4940a6d2b48d61fa7730
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

Loading…