HCID 13690971, compound → HCID 20230254, compound

HRID 2290777Notes

Reaction equation

HRID 2290777 reaction equation
Cl[CH2:2][CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1.[CH3:24][SH:25].[Na]>C(O)C>[F:22][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:9]([C:7]1[O:6][N:5]=[C:4]([CH2:3][CH2:2][S:25][CH3:24])[N:8]=1)[CH3:23]

Participants

4

Reactant 2

HCID 13690971HCID 13690971, compoundHCID 45051789Methylmercaptan sodium

Product 1

HCID 20230254HCID 20230254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.0 g of 3-(2-chloroethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole in 100 ml of ethanol was added 12.5 ml of 15% aqueous sodium methyl mercaptan. After stirring with reflux for 1 hour, the reaction mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed over silica gel using methylene chloride to give 4.78 g of 5-(3-fluoro-4-phenyl-α-methylbenzyl)-3-(2-methylthioethyl)-1,2,4-oxadiazole as a light yellow oil, nD21 1.5860.

Workup

  1. temperaturewith reflux for 1 hour
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-24f57a1e0b95454692809bc4994a1a2d
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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