Formamidine acetate → HCID 178419030, compound

HRID 6823

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

Conditions

Temperature: 110 °C

Procedure

Dimethylformamide (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

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 litres of ice water
customThe resulting precipitated solid
filtrationwas collected by suction filtration
washThe solid was washed with an additional one litre of distilled water
customThe resulting solid was dried under vacuum at 70° C.

Sources & evidence

ORD record: ord-0d4cdbe90b8748d0ab8949e429a5dc83
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084147B2

Linked notes

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