Thiophenol → HCID 20252648, compound

HRID 638575Notes

Reaction equation

HRID 638575 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:16])[N:11]=1.[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOCC.CC(C)=O>[C:24]1([S:30][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[O:16])[N:11]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 23320408HCID 23320408, compound

Product 1

HCID 20252648HCID 20252648, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 13.4 ml of triethylamine in 35 ml Et2O was added dropwise to a solution of 11.4 g of 5-chloromethyl-3-(4-toluoyl)-1,2,4-oxadiazole and 4.9 ml of thiophenol in 25 ml acetone and 100 ml Et2O at room temperature. The resulting mixture was stirred for one hour. The reaction mixture was diluted with Et2O, washed with 5% HCl (2×), water (2×), and brine, and dried over MgSO4. Concentration gave 13.2 g of an oil. Purification by high pressure liquid chromatography with 70% CH2Cl2 /hexane as an eluent yielded 11.0 g (79%) of an oil.

Workup

  1. washwashed with 5% HCl (2×), water (2×), and brine
  2. dry with materialdried over MgSO4
  3. concentrationConcentration

Sources & evidence

ORD record
ord-adbe9dd9c6c74ff29c1384a7efdf3842
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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