Hydrochloric Acid → HCID 178467952, compound

HRID 1482972Notes

Reaction equation

HRID 1482972 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3](=[O:8])[CH2:4][C:5](=[O:7])[CH3:6].[NH2:11][C:12]([NH2:14])=[O:13].[CH:15](OCC)(OCC)OCC.CO[Na].Cl>C(O)C>[C:5](/[C:4](/[C:3](=[O:8])[C:2]([F:10])([F:9])[F:1])=[CH:15]\[NH:11][C:12]([NH2:14])=[O:13])(=[O:7])[CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1176UreaHCID 31214Ethyl orthoformateHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 178418582HCID 178418582, compound

Product 1

HCID 178467952HCID 178467952, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,1,1-trifluoropentane-2,4-dione (200 g, 1.30 mol) in ethanol (200 mL) were added urea (78 g, 1.30 mol) and CH(OEt)3 (211.5 g, 1.43 mol). The mixture was stirred at 80° C. for 4 h. The resulting slurry was filtered. The filter cake was suspended in methanol (300 mL) and MeONa (77.2 g, 1.43 mol) was added. The mixture was stirred at reflux for 5 h, followed by slow addition of HCl (4N) to pH 3 at rt. The resulting slurry was filtered and the filter cake was dried under vacuum to give compound (E)-1-(2-acetyl-4,4,4-trifluoro-3-oxobut-1-en-1-yl)urea (196 g, 67.3% yield) as a white solid. 1H NMR (DMSO-d6 300 MHz): (Z/E) δ 10.15-10.13 (m, 1H), 8.64 (s, 1H), 7.69-7.66 (m, 2H), 2.25 (s, 3H). LC-MS MS (ESI) m/z 206.8 [M−18+H]+.

Workup

  1. filtrationThe resulting slurry was filtered
  2. stirringThe mixture was stirred
  3. temperatureat reflux for 5 h
  4. filtrationThe resulting slurry was filtered
  5. customthe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-a310877b26034aeaba1185816ddca612
Source dataset
uspto-grants-2016_08
Patent number
US09416135B2

Reaction notes

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