Propylamine → HCID 70050531, compound

HRID 247127Notes

Reaction equation

HRID 247127 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1)[C:2]([CH3:4])=O.[CH2:12]([NH2:15])[CH2:13][CH3:14]>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH2:12]([NH:15][C:2]([CH3:4])=[CH:1][C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1)[CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 7852PropylamineHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Product 1

HCID 70050531HCID 70050531, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent

Procedure

To a stirred solution of 350 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole in 10 ml of dry benzene-ether (3:1) was added dropwise with ice-cooling a solution of 190 mg of titanium tetrachloride in 1 ml of dry benzene. After the mixture was stirred for 1 hour, there was added dropwise 360 mg of n-propylamine with ice-cooling. The stirring was continued for 3 hours and then at room temperature for additional 3 hours. After the filtration of the reaction mixture, the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel using benzene-acetonitrile (10:1) as eluent to give 5-[2-(n-propylamino)-1-propenyl]-3-chloromethyl-1,2,4-oxadiazole as an oil.

Workup

  1. temperaturecooling
  2. waitThe stirring was continued for 3 hours
  3. waitat room temperature for additional 3 hours
  4. filtrationAfter the filtration of the reaction mixture
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-157b993b8129411e960b23f7b646f10f
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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