Water → N-Butyl-N-(4,5-diphenyl-1,3-oxazol-2-YL)-2-methylpropanamide

HRID 613988Notes

Reaction equation

HRID 613988 reaction equation
[CH2:1]([C:5](C)([CH3:9])[C:6]([NH2:8])=[O:7])CCC.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[C:16]1([C:22]2[N:23]=[C:24](I)[O:25][C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C1COCC1.CCCCCC>[CH2:11]([N:8]([C:24]1[O:25][C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]=1)[C:6](=[O:7])[CH:5]([CH3:9])[CH3:1])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 181100Hexanamide, 2,2-dimethyl-HCID 213297184,5-Diphenyl-2-iodooxazoleHCID 178418339Butyllithium

Product 1

HCID 21329726N-Butyl-N-(4,5-diphenyl-1,3-oxazol-2-YL)-2-methylpropanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl-isobutyramide (2.06 g, 0.0144 m) in dry THF (20 ml) was stirred at room temperature during the dropwise addition of a 1.445 M solution of n-butyl lithium in hexane (10.0 ml., 0.01445 m). After the addition, the mixture was stirred for 5 minutes, and then 4,5-diphenyl-2-iodooxazole (Chemical Abstracts 65 7159h) (5.0 g, 0.0144 m) in dry THF (20 ml) was added dropwise. The mixture was stirred for 6 hours at room temperature and then hydrolysed with water. The solvent was removed in vacuo and the residue extracted with diethyl ether.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred for 6 hours at room temperature
  3. customThe solvent was removed in vacuo
  4. extractionthe residue extracted with diethyl ether

Sources & evidence

ORD record
ord-7a955fc1eea549f39ac34daf0c89c0fe
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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