Ethyl 4,4,4-trifluoroacetoacetate → HCID 178516148, compound

HRID 1637778Notes

Reaction equation

HRID 1637778 reaction equation
C[O-].[Na+].CO.[NH2:6][C:7]([NH2:9])=[S:8].[F:10][C:11]([F:21])([F:20])[C:12](=O)[CH2:13][C:14](OCC)=[O:15]>C(O)C>[OH:15][C:14]1[CH:13]=[C:12]([C:11]([F:21])([F:20])[F:10])[N:9]=[C:7]([SH:8])[N:6]=1

Participants

5

Reactant 3

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2723790ThioureaHCID 23694274Sodium methanolate methanol

Product 1

HCID 178516148HCID 178516148, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 25% NaOMe/MeOH (23 ml, 0.10 mol) and ethanol (27 ml) are added thiourea (5.33 g, 0.70 mol) and ethyl 4,4,4-trifluoroacetoacetate (7.3 ml, 50 mmol), then the reaction is heated to reflux for 16 hrs. The mixture is cooled to 22° C., concentrated in vacuo, and the residue dissolved in water (50 ml), acidified with HCl (7 ml), and filtered. The solid is collected, washed with water, and dried: 6.58 g (32.5 mmol, 65%).

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 16 hrs
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved in water (50 ml)
  5. filtrationfiltered
  6. customThe solid is collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-bf425fe683ba4095b658b1838b9ec98c
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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