Ethyl Acetate → HCID 4397989, compound

HRID 1029535Notes

Reaction equation

HRID 1029535 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][C:6]([C:9]1[CH:10]=[C:11]([CH2:20][CH2:21][C:22]([NH:24][NH2:25])=[O:23])[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>[CH3:19][C:16]([C:13]1[CH:12]=[C:11]([CH2:20][CH2:21][C:22]2[O:23][C:1](=[S:2])[NH:25][N:24]=2)[CH:10]=[C:9]([C:6]([CH3:5])([CH3:7])[CH3:8])[C:14]=1[OH:15])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 4397989HCID 4397989, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiophosgene (0.55 mL, 6.80 mmol) is added dropwise to a -78° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid hydrazide (2.0 g, 6.8 mmol) in tetrahydrofuran (200 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. The product is chromatographed on a column of silica with ethyl acetate/dichloromethane (5/95) and recrystallized from dichloromethane/hexane to afford 0.36 g (16%) of 5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethyl]-1,3,4-oxadiazole-2(3H)-thione, mp 164.5°-165.5° 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
  7. customThe product is chromatographed on a column of silica with ethyl acetate/dichloromethane (5/95)
  8. customrecrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-060fe457371645a99232a6173ff849ba
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

Loading…