Water → HCID 22325512, compound

HRID 987516Notes

Reaction equation

HRID 987516 reaction equation
[Na].C([O:4][C:5](=O)[CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[C:7](OCC)=[O:8])C.[NH2:20][C:21]([NH2:23])=[S:22].O>C(O)C>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:6]1[C:5](=[O:4])[NH:23][C:21](=[S:22])[NH:20][C:7]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 2723790ThioureaHCID 5360545Sodium2×HCID 22325508HCID 22325508, compound

Product 1

HCID 22325512HCID 22325512, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To absolute ethanol (200 ml), sodium (3.62 g, 157 mmol) was added at room temperature under nitrogen atmosphere. The reaction mixture was stirred until all the sodium had reacted A solution of diethyl-(2-fluorophenyl)malonate (20 g, 78.7 mmol) in absolute ethanol (50 ml) was then added followed by thiourea (8.38 g, 110 mmol). The reaction mixture was then refluxed under nitrogen atmosphere for 17 hours. The cooled reaction mixture was then poured into water (800 ml), the reswiting mixture stirred for 15 minutes and extracted with diethyl ether (500 ml) The organic phase was extracted with brine (150 ml, ⅓ saturated) and the aqueous layers combined. Now concentrated hydrochloric acid (14 ml) was added to the aqueous phase and the resulting white suspension was stirred gently for 1 hour. The suspension was filtered and the resulting solid washed with water, followed by diethyl ether and dried in vacuo for approximately 12 hours to afford 8.59 g (46% yield) of the title compound as a white solid (melting point: >240° C.).

Workup

  1. additionwas then added
  2. temperatureThe reaction mixture was then refluxed under nitrogen atmosphere for 17 hours
  3. customThe cooled reaction mixture
  4. extractionextracted with diethyl ether (500 ml) The organic phase
  5. extractionwas extracted with brine (150 ml, ⅓ saturated)
  6. additionNow concentrated hydrochloric acid (14 ml) was added to the aqueous phase
  7. stirringthe resulting white suspension was stirred gently for 1 hour
  8. filtrationThe suspension was filtered
  9. washthe resulting solid washed with water
  10. customdried in vacuo for approximately 12 hours

Sources & evidence

ORD record
ord-9939624928e2466dbefbd51e554b6da3
Source dataset
uspto-grants-2003_10
Patent number
US06632821B2

Reaction notes

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