Formamidine acetate → HCID 178419030, compound

HRID 585607Notes

Reaction equation

HRID 585607 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]>>[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

3

Reactant 2

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

Product 1

HCID 178419030HCID 178419030, compoundYield 91.2%

Conditions

Temperature
110 °C

Procedure

Dimethylfornamide (0.5 litres), 4-fluoro-5-iodo-isatoic anhydride (45 grams, 147 mmoles), and formamidine acetate (45.92 grams, 441 mmoles), were combined in a one litre 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 litres of ice water. The resulting precipitated solid was collected by suction filtration. The solid was washed with an additional one litre 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 litres of ice water
  6. customThe resulting precipitated solid
  7. filtrationwas collected by suction filtration
  8. washThe solid was washed with an additional one litre of distilled water
  9. customThe resulting solid was dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-1f77beed3f3c40259308684d05e73270
Source dataset
uspto-grants-2005_08
Patent number
US06933299B1

Reaction notes

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