Water → N-Butyl-N-(4-methyl-1,3-oxazol-2-yl)-2-phenylacetamide

HRID 613993Notes

Reaction equation

HRID 613993 reaction equation
[CH2:1]([NH:5][C:6](=[O:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].C1(S([C:25]2[O:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=O)CCCCC1.O>CN1CCCC1=O.CCOCC>[CH2:1]([N:5]([C:25]1[O:26][CH:27]=[C:28]([CH3:30])[N:29]=1)[C:6](=[O:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 221447N-butyl-2-phenylacetamideHCID 213297332-(Cyclohexanesulfinyl)-4-methyl-1,3-oxazole

Product 1

HCID 12556859N-Butyl-N-(4-methyl-1,3-oxazol-2-yl)-2-phenylacetamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
100 °C

Procedure

N-Butyl-phenylacetamide (1.80 g, 0.0094 m) in N-methyl pyrrolidone (10 ml) was stirred at 80° C. under nitrogen during the portionwise addition of a 50% sodium hydride/oil dispersion (0.75 g, 0.0094 m). After the addition, the mixture was warmed to 100° C. and 2-cyclohexylsulphinyl-4-methyloxazole (2.0 g, 0.0094 m) in dry N-methyl pyrrolidone (10 ml) was added. The mixture was stirred at 100° C. for 5 hours and then hydrolysed with water. The solvent was removed in vacuo and the product isolated by column chromatography on silica using ether. Distillation gave the title product as a colourless oil. b.p. 126°-130° C./0.2 mm.

Workup

  1. additionAfter the addition
  2. customThe solvent was removed in vacuo
  3. customthe product isolated by column chromatography on silica
  4. distillationDistillation

Sources & evidence

ORD record
ord-69f89adf066c4a4587607b93a1abb292
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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