Acetone → HCID 20252656, compound

HRID 638573Notes

Reaction equation

HRID 638573 reaction equation
C(N(CC)CC)C.[C:8]([C:16]1[N:20]=[C:19]([CH2:21]Cl)[O:18][N:17]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC(C)=O>CCOCC>[C:8]([C:16]1[N:20]=[C:19]([CH2:21][S:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:18][N:17]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7969ThiophenolHCID 8471TriethylamineHCID 20252653HCID 20252653, compound

Product 1

HCID 20252656HCID 20252656, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 11.4 ml of triethylamine in 30 ml Et2O was added dropwise to a solution consisting of 9.0 g of 3-benzoyl-5-chloromethyl-1,2,4-oxadiazole, 4.2 ml of thiophenol, 20 ml of acetone and 80 ml of 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 11.5 g of an oil. Purification by high pressure liquid chromatography with 70% CH2Cl2 /hexane as an eluent yielded 10.3 g (84%) 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-0293fbbd703848908d7bdf61d63c2613
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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