Ethyl Acetate → HCID 19900647, compound

HRID 1029529Notes

Reaction equation

HRID 1029529 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][C:6]([C:9]1[CH:10]=[C:11]([S:20][CH2:21][CH2:22][C:23]([NH:25][NH2:26])=[O:24])[CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=1[OH:15])([CH3:8])[CH3:7].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:8][C:6]([C:9]1[CH:10]=[C:11]([S:20][CH2:21][CH2:22][C:23]2[O:24][C:1](=[S:2])[NH:26][N:25]=2)[CH:12]=[C:13]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:14]=1[OH:15])([CH3:5])[CH3:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 19609556HCID 19609556, compound

Product 1

HCID 19900647HCID 19900647, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiophosgene (0.34 mL, 4.40 mmol) is added dropwise to a -78° C. solution of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoic acid hydrazide (1.5 g, 4.40 mmol) in tetrahydrofuran (150 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and aqueous sodium bicarbonate. The organic phase is washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a heavy oil which is crystallized from ethyl acetate/hexane to afford 1.0 g (59%) of 5-[2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]ethyl]-1,3,4-oxadiazole-2(3H)-thione, mp 123.5°-124.5° C.

Workup

  1. additionthen poured into a separatory funnel
  2. washThe organic phase is washed three times with water
  3. customDrying the organic phase
  4. customover magnesium sulfate and evaporation
  5. customgives a heavy oil which
  6. customis crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-29ce98242a8943e4b9042fb73de64fe8
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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