2,2,3,3,3-Pentafluoropropylamine → 4-[3,4-Dioxo-2-(2,2,3,3,3-pentafluoro-propylamino)cyclobut-1-enylamino]-benzonitrile

HRID 128764Notes

Reaction equation

HRID 128764 reaction equation
[O:1]=[C:2]1[C:5](=O)[C:4]([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[C:3]1[O:16]CC.[F:19][C:20]([F:27])([C:23]([F:26])([F:25])[F:24])[CH2:21][NH2:22]>C(O)C>[O:1]=[C:2]1[C:3](=[O:16])[C:4]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)=[C:5]1[NH:22][CH2:21][C:20]([F:27])([F:19])[C:23]([F:26])([F:25])[F:24]

Participants

4

Reactant 2

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 108240584-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

Product 1

HCID 194369754-[3,4-Dioxo-2-(2,2,3,3,3-pentafluoro-propylamino)cyclobut-1-enylamino]-benzonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(3,4-Dioxo-2-ethoxy-cyclobut-1-enylamino)-benzonitrile (1 g, 4.1 mmol) and 2,2,3,3,3-pentafluoropropylamine (3 mL) in ethanol were refluxed for 24 hours. The reaction mixture was filtered and the resulting solid was triturated with diethyl ether to give 1.0 g (71%) of 4-[3,4-dioxo-2-(2,2,3,3,3-pentafluoro-propylamino)cyclobut-1-enylamino]-benzonitrile as a yellow solid: mp 272°-275° C. (dec); 1H NMR (DMSO-d6): δ10.15 (br s, 1H), 8.19 (br s, 1H), 7.81 (d, 2H), 7.79 (d, 2H), 4.54 (dr, 2H). IR (KBr): 3185, 2239, 1804, 1672, 1608, 1565, 1548 cm-1 ; MS (m/z) 346 ([M+H]+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-7be71a757e6f46c7a9cf0d005c054649
Source dataset
uspto-grants-1995_11
Patent number
US05464867

Reaction notes

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