Thiourea → HCID 178522471, compound

HRID 1507773Notes

Reaction equation

HRID 1507773 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[F:5][C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][CH:13]([C:19](OCC)=[O:20])[C:14](OCC)=[O:15])=[O:11])=[CH:8][CH:7]=1.[Na]>C(O)C>[OH:20][C:19]1[C:13]([NH:12][C:10](=[O:11])[C:9]2[CH:24]=[CH:25][C:6]([F:5])=[CH:7][CH:8]=2)=[C:14]([OH:15])[N:4]=[C:2]([SH:3])[N:1]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 5360545SodiumHCID 33239760HCID 33239760, compound

Product 1

HCID 178522471HCID 178522471, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (0.72 g, 9.4 mmol) and diethyl 2-(4-fluorobenzamido)malonate (example 1, 2.0 g, 6.7 mmol) were added to a solution of sodium (0.16 g, 6.7 mmol) in ethanol (50 ml). The reaction mixture was refluxed for 3 hours and then cooled down to room temperature. The precipitate was filtered off and washed with ethanol. The product was dissolved in a minimal volume of water and acidified to pH 4-5 with 5M HCl. The precipitate was collected, washed with water and dried, furnishing the title compound as a white solid (0.78 g, 41%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. filtrationThe precipitate was filtered off
  3. washwashed with ethanol
  4. dissolutionThe product was dissolved in a minimal volume of water
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0796852cfff74bbf9415a512c9b83bd6
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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