Carbon Dioxide → HCID 21313000, compound

HRID 971702Notes

Reaction equation

HRID 971702 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]1[N:18]=[C:17]([CH3:19])[O:16][N:15]=1.CN(CCN(C)C)C.[C:28](=[O:30])=[O:29].Cl>CCCCCC.C1(C)C=CC=CC=1.O.C(OCC)C>[Cl:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[C:8]=1[C:14]1[N:18]=[C:17]([CH2:19][C:28]([OH:30])=[O:29])[O:16][N:15]=1

Participants

10

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 213129273-(2,6-Dichlorophenyl)-5-methyl-1,2,4-oxadiazoleHCID 178418339Butyllithium

Product 1

HCID 21313000HCID 21313000, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of an approximately equivalent amount of n-butyl lithium in 22.2 ml of n-hexane was added dropwise to a solution of 10 g of 3-(2,6-dichlorophenyl)-5-methyl-1,2,4-oxadiazole (m.p. 83°-85° C.) and 6.4 ml of TMEDA in 140 ml of dry toluene using the procedure of Example 1 over a period of about 30 minutes. The reaction temperature was -55° to -60° C. After stirring the reaction mixture for another hour at about -60° C. the mixture was added to powdered carbon dioxide covered with dry diethyl ether. After standing a few hours, water and dilute hydrochloric acid were added until a pH of 8.0 was reached. The layers were separated, and the organic layer was extracted with 50 ml of water. The organic layer was discarded and the combined aqueous layers of about 300 ml were washed twice with 100 ml of diethyl ether. Then, the aqueous layer was extracted three times with 100 ml portions of diethyl ether at a pH of 2.0 These extracts were combined, washed twice with a small amount of ice-water and completely evaporated in vacuo. The solid residue was stirred up first with n-heptane and then with a small volume of toluene. After extensive drying in the desiccator, the final product of 3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl-acetic acid weighed 7.6 g (63% yield) and had a m.p. of 124.5°-125.5° C.

Workup

  1. customwas -55° to -60° C
  2. additionwas added
  3. waitAfter standing a few hours
  4. customThe layers were separated
  5. extractionthe organic layer was extracted with 50 ml of water
  6. washthe combined aqueous layers of about 300 ml were washed twice with 100 ml of diethyl ether
  7. extractionThen, the aqueous layer was extracted three times with 100 ml portions of diethyl ether at a pH of 2.0 These extracts
  8. washwashed twice with a small amount of ice-water
  9. customcompletely evaporated in vacuo
  10. stirringThe solid residue was stirred up first with n-heptane
  11. customAfter extensive drying in the desiccator

Sources & evidence

ORD record
ord-7c21ea13fc83443eaf57ae1a5b578d0d
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

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