Sodium hydride → HCID 67266739, compound

HRID 602777Notes

Reaction equation

HRID 602777 reaction equation
[OH:1][NH:2][C:3](=[NH:5])[CH3:4].[H-].[Na+].C(O[C:11](=O)[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C>C1COCC1.[NH4+].[Cl-]>[CH3:4][C:3]1[N:5]=[C:11]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:1][N:2]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 97312Acetic acid, (phenylthio)-, ethyl esterHCID 178465666HCID 178465666, compound

Product 1

HCID 67266739HCID 67266739, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

565 mg (7.65 mmol, 1.5 eq) of N-hydroxy-acetamidine in 50 ml of THF were treated at RT with 306 mg (7.65 mmol, 1.5 eq) of NaH portionwise within 30 min. 1.0 g (5.1 mmol) of phenylsulfanyl-acetic acid ethyl ester was added in a THF solution, and stirring was continued for 1 hour at 60° C. The reaction mixture was diluted with saturated aqueous NH4Cl, extracted with EtOAc, filtered and evaporated. Column chromatography on silica gel with EtOAc/heptane 1:1 yielded 480 mg (46%) of 3-methyl-5-phenylsulfanylmethyl-[1,2,4]oxadiazole as a colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-cf7dc52920de495198fe4924149e2de9
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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