Chloroacetyl chloride → 5-(Chloromethyl)-3-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole

HRID 848179Notes

Reaction equation

HRID 848179 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]([CH3:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][CH2:15][C:16](=[N:18]O)[NH2:17].C(N(CC)CC)C>C1C=CC=CC=1.CCOCC.C(=O)(O)[O-].[Na+]>[Cl:1][CH2:2][C:3]1[O:4][N:17]=[C:16]([CH2:15][S:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([CH3:20])[CH3:6])[N:18]=1

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 541832962-(2-Dimethylaminophenylthio)acetamidoxime

Product 1

HCID 205663795-(Chloromethyl)-3-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Chloroacetylchloride (2.64 ml, 3.74 g, 3.3×10-2 mol) in benzene (10 ml) was added dropwise to a stirred solution of 2-(2-dimethylaminophenylthio)acetamidoxime (6.75 g, 0.03 mol) and triethylamine (4.17 ml) in benzene (20 ml). The mixture was stirred at ambient temperature for 10 hours then refluxed for 1 hour. The cooled mixture was taken up in ether and 5% aqueous sodium bicarbonate solution. The organic layer was washed with water and saturated aqueous sodium chloride solution dried and evaporated to dryness to give a brown oil. Chromatography on silica gel (135 g), eluting with hexane:ether (3:1) gave 5-(chloromethyl)-3-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole as a colourless oil, nmr δ(CDCl3) 2.78(6H, CH3), 4.20(2H, ,--CH2 --), 4.65 (2H, ,--CH2 --), 6.8-7.4 (4H, m, aromatic hydrogens).

Workup

  1. temperaturethen refluxed for 1 hour
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  3. customdried
  4. customevaporated to dryness
  5. customto give a brown oil
  6. washChromatography on silica gel (135 g), eluting with hexane:ether (3:1)

Sources & evidence

ORD record
ord-4e1e0311810347c98f52784a7f7dc5c0
Source dataset
uspto-grants-1981_10
Patent number
US04294843

Reaction notes

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