Ethyl Acetate → HCID 19900665, compound

HRID 1029523Notes

Reaction equation

HRID 1029523 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH:5]([C:7](=[O:24])[S:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=1)[NH2:6].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:23][C:20]([C:11]1[CH:10]=[C:9]([S:8][C:7]2[O:24][C:1](=[S:2])[NH:6][N:5]=2)[CH:14]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:12]=1[OH:19])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 19900651HCID 19900651, compound

Product 1

HCID 19900665HCID 19900665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiophosgene (0.39 mL, 5.1 mmol) is added dropwise to a -78° C. solution of S-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl] hydrazinecarbothioate (1.5 g, 5.1 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 solid which is crystallized from dichloromethane/hexane affording 1.1 g (62%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1,3,4-oxadiazole-2(3H)-thione, mp 129.0°-131.0° 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 solid which
  6. customis crystallized from dichloromethane/hexane affording 1.1 g (62%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1,3,4-oxadiazole-2(3H)-thione, mp 129.0°-131.0° C.

Sources & evidence

ORD record
ord-02de17e98f884b848a7667915f7743b4
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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