Formamidine acetate → HCID 178419030, compound

HRID 2215690Notes

Reaction equation

HRID 2215690 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=O)O[C:6](=[O:7])[C:5]2=[CH:12][C:13]=1[I:14].C(O)(=O)C.C(N)=[NH:20]>CN(C)C=O>[OH:7][C:6]1[C:5]2[C:4](=[CH:3][C:2]([F:1])=[C:13]([I:14])[CH:12]=2)[N:10]=[CH:9][N:20]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 543357764-Fluoro-5-iodo-isatoic Anhydride

Product 1

HCID 178419030HCID 178419030, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Dimethylformamide (0.5 liters), 4-fluoro-5-iodo-isatoic anhydride (45 grams, 147 mmoles), and formamidine acetate (45.92 grams, 441 mmoles), were combined in a one liter one-neck flask fitted with a magnetic stir bar. The mixture was placed under anhydrous nitrogen and heated at 110° C. for 6 hours. The mixture was allowed to cool, followed by concentrating the reaction mixture to one third its original volume on the rotary evaporator. The resulting mixture was poured onto 3 liters of ice water. The resulting precipitated solid was collected by suction filtration. The solid was washed with an additional one liter of distilled water. The resulting solid was dried under vacuum at 70° C. to yield 38.9 grams (91%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 12.43(s, 1H), 8.46(d, 1H), 8.12(s, 1H), 7.49(d, 1H). ESI-MS m/z 291 (M+1).

Workup

  1. customfitted with a magnetic stir bar
  2. temperatureto cool
  3. concentrationby concentrating the reaction mixture to one third its original volume
  4. customon the rotary evaporator
  5. additionThe resulting mixture was poured onto 3 liters of ice water
  6. customThe resulting precipitated solid
  7. filtrationwas collected by suction filtration
  8. washThe solid was washed with an additional one liter of distilled water
  9. customThe resulting solid was dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-292c095b1aa04e2582223acc6633946c
Source dataset
uspto-grants-2006_09
Patent number
US07109333B2

Reaction notes

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