Formamidine acetate → HCID 178419030, compound
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]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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, 1 H). ESI-MS m/z 291 (M+1).
Workup
- customfitted with a magnetic stir bar
- temperatureto cool
- concentrationby concentrating the reaction mixture to one third its original volume
- customon the rotary evaporator
- additionThe resulting mixture was poured onto 3 liters of ice water
- customThe resulting precipitated solid
- filtrationwas collected by suction filtration
- washThe solid was washed with an additional one liter of distilled water
- customThe resulting solid was dried under vacuum at 70° C.
Sources & evidence
- ORD record
- ord-ee5609a045124d56a8e68d3dfd2aee8f
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189734B2
Reaction notes
Loading…