Thiourea → HCID 178499520, compound

HRID 2292566Notes

Reaction equation

HRID 2292566 reaction equation
CN(C)[CH:3]=[CH:4][C:5](=O)[CH:6]([O:9][CH3:10])[O:7][CH3:8].[NH2:13][C:14]([NH2:16])=[S:15].C[O-].[K+]>CC(O)C>[CH3:8][O:7][CH:6]([O:9][CH3:10])[C:5]1[CH:4]=[CH:3][NH:16][C:14](=[S:15])[N:13]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneHCID 23664618Potassium methoxide

Product 1

HCID 178499520HCID 178499520, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The product from step 1 (4.8 g), thiourea (2.53 g) and potassium methylate (2.33 g) were heated together in boiling propan-2-ol (30 cm3) for 6 hours. The reaction mixture was allowed to cool overnight. The solvent was removed by evaporation under reduced pressure, the residue was dissolved in water and washed with ethyl acetate, the organic layer being discarded. The basic aqueous layer was acidified to pH 5 using glacial acetic acid and the product was extracted into ethyl acetate. Evaporation of the ethyl acetate under reduced pressure gave 3.769 g of an orange oil. 1H NMR (DMSO): δ3.46(6H,s); 5.14(1H,s); 6.94(1H,d); 7.18(1H,br s); 8.18(1H,d).

Workup

  1. customfor 6 hours
  2. temperatureto cool overnight
  3. customThe solvent was removed by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washwashed with ethyl acetate
  6. extractionthe product was extracted into ethyl acetate
  7. customEvaporation of the ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-a45f456ecb6e4c128092030274d6b16a
Source dataset
uspto-grants-1997_11
Patent number
US05684011

Reaction notes

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