Triethylamine → HCID 13591725, compound

HRID 1380533Notes

Reaction equation

HRID 1380533 reaction equation
[CH3:1][C:2]1([C:5]2[O:6][C:7](=[O:10])[NH:8][N:9]=2)[CH2:4][CH2:3]1.[C:11]1([Sn:17](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1([C:5]2[O:6][C:7](=[O:10])[N:8]([Sn:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12540Triphenyltin ChlorideHCID 127870775-(1-Methylcyclopropyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 13591725HCID 13591725, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 5 g (0.035 mole) 2-(1'-methylcyclopropyl)-5-oxo-1,3,4-oxadiazoline and 13.5 g (0.035 mole) triphenyl tin chloride in methylene chloride (about 100 ml), 3.5 g (0.035 mole) triethylamine in methylene chloride (about 50 ml) was added dropwise. The reaction mixture was allowed to stir overnight at ambient temperature. The reaction mixture was refluxed (at about 40° C.) for about 3 hours, cooled and then allowed to stir at ambient temperature for about one hour. The reaction mixture was washed with water and then extracted with methylene chloride. The methylene chloride extract was dried and then stripped. The residue was washed with hexane to precipitate the above-identified product, melting point 165°-167° C.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was refluxed (at about 40° C.) for about 3 hours
  3. temperaturecooled
  4. stirringto stir at ambient temperature for about one hour
  5. washThe reaction mixture was washed with water
  6. extractionextracted with methylene chloride
  7. extractionThe methylene chloride extract
  8. customwas dried
  9. washThe residue was washed with hexane
  10. customto precipitate the above-identified product, melting point 165°-167° C.

Sources & evidence

ORD record
ord-cbd1fcceebba43af91224be34d6c5ee3
Source dataset
uspto-grants-1986_04
Patent number
US04582828

Reaction notes

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