1,1'-Carbonyldiimidazole → Ethyl alpha-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-3,3-dimethylbutanoate

HRID 355336Notes

Reaction equation

HRID 355336 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6](O)=[O:7])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][C:27]1[S:31][C:30](=[S:32])[NH:29][N:28]=1>C1COCC1>[S:32]=[C:30]1[S:31][C:27]([NH:26][C:6]([CH:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]([O:3][CH2:1][CH3:2])=[O:13])=[O:7])=[N:28][NH:29]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27238472-Amino-5-mercapto-1,3,4-thiadiazoleHCID 109432282-(Ethyl carboxy)-3,3-dimethylbutanoic acid

Product 1

HCID 54237532Ethyl alpha-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-3,3-dimethylbutanoateYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butylmalonic acid monoethyl ester (3.0 g, 16.0 mmol) in THF (100 mL) is added carbonyldiimidazole (2.85 g, 17.6 mmol) and the reaction is stirred overnight. 5-Amino-(3H)-1,3,4-thiadiazole-2-thione (864 mg, 6.5 mmol) is added and stirring continued for an additional 72 hours. The reaction mixture is 35 poured into pH 4 buffer, extracted with methylene chloride, and the organic layers combined, dried (anhydrous sodium sulfate) and concentrated. Chromatography of the residue on silica gel (elution with 5% methanol/methylene chloride) gave 1.2 g (25%) of the title compound as an amorphous solid.

Workup

  1. stirringstirring
  2. waitcontinued for an additional 72 hours
  3. additionpoured into pH 4 buffer
  4. extractionextracted with methylene chloride
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f48fcae321741eb9ef9c054abb3533a
Source dataset
uspto-grants-1998_11
Patent number
US05830869

Reaction notes

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