Ethyl Acetate → HCID 19900654, compound

HRID 1029525Notes

Reaction equation

HRID 1029525 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH:5]([C:7]([S:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=1)=[S:8])[NH2:6].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:24][C:21]([C:12]1[CH:11]=[C:10]([S:9][C:7]2[S:8][C:1](=[S:2])[NH:6][N:5]=2)[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:13]=1[OH:20])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 54090446HCID 54090446, compound

Product 1

HCID 19900654HCID 19900654, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiophosgene (0.37 mL, 4.8 mmol) is added dropwise to a -78° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl hydrazinecarbodithioate (1.5 g, 4.8 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 ethyl acetate/hexane to afford 1.5 g (88%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1,3,4thiadiazole-2(3H)-thione, mp 181.0°-185.5° 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 solid which
  6. customis crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-330e072a17f9448db7b550c2bf51f94a
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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