Sodium hydride → HCID 67267381, compound

HRID 602811Notes

Reaction equation

HRID 602811 reaction equation
[OH:1][NH:2][C:3](=[NH:7])[N:4]([CH3:6])[CH3:5].[H-].[Na+].C(O[C:13](=O)[CH2:14][S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C>C1COCC1>[CH3:5][N:4]([CH3:6])[C:3]1[N:7]=[C:13]([CH2:14][S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:1][N:2]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 97312Acetic acid, (phenylthio)-, ethyl esterHCID 178484392HCID 178484392, compound

Product 1

HCID 67267381HCID 67267381, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 14 g (0.129 mol, 1.4 eq) of 3-hydroxy-1,1-dimethyl-guanidine in 300 mL dry THF at 0° C. was added portionwise 6.191 g (0.155 mol, 1.2 eq) of NaH (60% in oil). The resulting heavy suspension was stirred at RT for 1 hour 30 minutes. Then, 28.126 g (0.129 mol) phenylsulfanyl-acetic acid ethyl ester were slowly added. The reaction mixture was stirred at RT for 2 hours and then at 65° C. for 1 hour. The reaction was quenched by addition of a saturated aqueous solution of NH4Cl and the product extracted with EtOAc. The combined organic phase was dried on Na2SO4, filtered and evaporated. Column chromatography on silica gel (EtOAc/heptane, 1:9 to 1:2) yielded 19.370 g (64%) dimethyl-(5-phenylsulfanylmethyl-[1,2,4]oxadiazol-3-yl)-amine as a colorless oil, MS: 236 (MH+).

Workup

  1. stirringThe reaction mixture was stirred at RT for 2 hours
  2. waitat 65° C. for 1 hour
  3. customThe reaction was quenched by addition of a saturated aqueous solution of NH4Cl
  4. extractionthe product extracted with EtOAc
  5. customThe combined organic phase was dried on Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-649aeed490144a5782c05d5b1d29f727
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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