Thiophenol → HCID 20252652, compound

HRID 638574Notes

Reaction equation

HRID 638574 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[N:19]=[C:18]([CH2:20]Cl)[O:17][N:16]=2)=[O:14])=[CH:11][CH:10]=1.[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOCC.CC(C)=O>[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[N:19]=[C:18]([CH2:20][S:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:17][N:16]=2)=[O:14])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 20252660HCID 20252660, compound

Product 1

HCID 20252652HCID 20252652, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 8.1 ml of triethylamine in 30 ml Et2O was added to a solution of 7.5 g of 3-(4-chlorobenzoyl)-5-chloromethyl-1,2,4-oxadiazole and 3.0 ml of thiophenol in 20 ml of acetone and 80 ml of Et2O at room temperature. This mixture was stirred for one hour. The reaction mixture was diluted with Et2O, washed with 5% HCl (2×) and brine, and dried over MgSO4. Concentration gave 9.0 g of an oil. Purification by high pressure liquid chromatography with 70% CH2CL2 /hexane as an eluent yielded 6.0 g (62%) of an oil.

Workup

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

Sources & evidence

ORD record
ord-dc880e4640744cd8aeb46f7cc8735fa6
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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