HCID 59416172, compound → HCID 18753050, compound

HRID 2061848Notes

Reaction equation

HRID 2061848 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH:10]=[C:11]([C:17]([O:19]CC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]2[C:3]=1[NH:9][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]2=[O:19]

Participants

3

Reactant 2

HCID 59416172HCID 59416172, compound2×HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 18753050HCID 18753050, compound

Conditions

Temperature
90 °C

Procedure

Diethyl 2-((2-fluoro-4-iodophenylamino)methylene)malonate (Intermediate 10, 13.45 g, 33.05 mmol) was placed in a 250 mL round bottom flask with Eaton's Reagent (55 mL, 0.29 mol) and aged while stirring at 90° C. for 4-5 days. The reaction was then cooled to 5° C. and was slowly quenched with saturated sodium carbonate solution (500 ml) at 10° C. to form a clumpy brownish-yellow solid. The precipitate was vacuum filtered and washed with water (300 ml). The collected solid was dried under vacuum at 50° C. for 16 h, resulting in 10.7 g (90%) of light tan solid.

Workup

  1. temperatureThe reaction was then cooled to 5° C.
  2. customwas slowly quenched with saturated sodium carbonate solution (500 ml) at 10° C.
  3. customto form a clumpy brownish-yellow solid
  4. filtrationfiltered
  5. washwashed with water (300 ml)
  6. customThe collected solid was dried under vacuum at 50° C. for 16 h
  7. customresulting in 10.7 g (90%) of light tan solid

Sources & evidence

ORD record
ord-c11f1b19910a44abb9ce649ce3d64c29
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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