Methyl Ethyl Ketone → 3-Benzyl-5-[2-(4-chlorophenyl)3-methyl butoxymethyl]1,2,4-oxadiazole

HRID 839617Notes

Reaction equation

HRID 839617 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13]Cl)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH:26]([CH3:28])[CH3:27])[C:23](O)=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C.CC(CC)=O>C1C=CC=CC=1>[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][O:24][CH2:23][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=2)[CH:26]([CH3:28])[CH3:27])[O:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 8471TriethylamineHCID 16197Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-HCID 80271323-Benzyl-5-(chloromethyl)-1,2,4-oxadiazole

Product 1

HCID 203238203-Benzyl-5-[2-(4-chlorophenyl)3-methyl butoxymethyl]1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

First, 2.1 grams (0.01 mole) of the intermediate of Example I, 2.3 grams (0.011 mole) of 2-(4-chlorophenyl)3-methyl butyric acid, 1.0 grams (0.01 mole) of triethylamine, and 100 milliliters of methylethylketone were combined and heated under reflux for 2 hours. The mixture was then cooled and poured into 200 milliliters of benzene. The benzene mixture was then washed in turn with 100 milliliters of H2O, 100 milliliters of 5% K2CO3 solution, and 100 milliliters of H2O. The benzene phase was then dried with MgSO4 and evaporated in vacuo to yield 3.0 grams (78% of theory) of the desired product. nD30 1.5210.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe mixture was then cooled
  4. washThe benzene mixture was then washed
  5. dry with materialThe benzene phase was then dried with MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b69e15e3eeb044e5ac6a5db3911b21ff
Source dataset
uspto-grants-1978_06
Patent number
US04096273

Reaction notes

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