Hydrazine hydrate (1:1) → 4-Amino-2-pentafluorosulfanylbenzonitrile

HRID 2080934Notes

Reaction equation

HRID 2080934 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20]([F:25])([F:24])([F:23])([F:22])[F:21])[CH:13]=1.[OH2:26].NN>C(O)C>[NH2:3][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20]([F:25])([F:21])([F:22])([F:23])[F:24])[CH:13]=1.[C:16]([C:15]1[CH:18]=[CH:19][C:12]([NH:3][C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O-:26])=[O:11])=[CH:13][C:14]=1[S:20]([F:21])([F:22])([F:25])([F:23])[F:24])#[N:17]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 596421514-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-2-pentafluorosulfanylbenzonitrile

Product 2

HCID 596421594-Amino-2-pentafluorosulfanylbenzonitrileHCID 86599508N-(4-cyano-3-pentafluorosulfanylphenyl)phthalamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

610 mg (1.63 mmol) of 4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-pentafluorosulfanylbenzonitrile (prepared in example 6) were dissolved in 30 ml of ethanol and admixed with 100 mg (1.956 mmol) of hydrazine hydrate (100%). The mixture was stirred at room temperature overnight. Afterward, the reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography (preparative HPLC; Purospher STAR RP-18e (10 μm); eluent: 5/95→95/5 [45 min.] acetonitrile/water (0.5% trifluoroacetic acid)). 4-Amino-2-pentafluorosulfanylbenzonitrile (1H NMR (500 MHz; d6-dmso) δ [ppm]=7.65 (s, 1H); 7.2 (s, 1H, 6.8 (m, 3H)) and N-(4-cyano-3-pentafluorosulfanylphenyl)phthalamate (1H NMR (500 MHz; d6-dmso) δ [ppm]=11.3 (s, 1H); 8.6 (s, 1H); 8.2 (d, 1H); 8.1 (d, 1H); 7.95 (d, 1H); 7.75 (m, 1H); 7.7 (m, 2H); 4.2 (q, 2H); 1.15 (t, 3H)) were obtained.

Workup

  1. concentrationAfterward, the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography (preparative HPLC; Purospher STAR RP-18e (10 μm); eluent: 5/95→95/5 [45 min.] acetonitrile/water (0.5% trifluoroacetic acid))

Sources & evidence

ORD record
ord-c9cd23be476b42018cd8e260052ca2f6
Source dataset
uspto-grants-2011_04
Patent number
US07932416B2

Reaction notes

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