Hydrochloric Acid → HCID 21312991, compound

HRID 971710Notes

Reaction equation

HRID 971710 reaction equation
Cl.[CH2:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:10][C:11]1[N:15]=[C:14]([CH2:16][C:17](O)=[O:18])[O:13][N:12]=1>O>[CH3:10][C:11]1[N:15]=[C:14]([CH2:16][C:17]([O:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:18])[O:13][N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8129HeptanolHCID 213130182-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid

Product 1

HCID 21312991HCID 21312991, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under anhydrous conditions, a stream of gaseous hydrochloric acid was passed through 25 ml of n-heptanol and as soon as a saturated solution was reached at room temperature, 5.7 g (0.04 mol) of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid were introduced. Introduction of a slow stream of hydrochloric acid was continued for two hours and the reaction mixture was then stirred for 60 hours at room temperature whereby conversion of the carboxylic acid was virtually completed. The reaction mixture was thoroughly mixed with 75 ml of cold water and the layers were separated. The organic layer was washed three times with 10 ml volumes of a saturated solution of sodium bicarbonate in water, and two times with 10 ml of cold water. All water-layers were combined and extracted twice with 20 ml volumes of ethyl acetate. The combined ethyl acetate extracts were once washed with 10 ml of iced water and the water-layers were discarded. The two organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was distilled and fractionated at reduced pressure to obtain 6.8 g of n-heptyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate of about 95% molar purity (impurity mainly a small amount of n-heptanol with a b.p. of 108° C. at 0.25 mm Hg and a refractive index nD20 =1.450.

Workup

  1. customwas reached at room temperature
  2. customthe layers were separated
  3. washThe organic layer was washed three times with 10 ml volumes of a saturated solution of sodium bicarbonate in water, and two times with 10 ml of cold water
  4. extractionextracted twice with 20 ml volumes of ethyl acetate
  5. washThe combined ethyl acetate extracts were once washed with 10 ml of iced water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-8f77d5684c3d437088968d0e68106d3d
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

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