2-Fluorobenzonitrile → 2-(4-Trifluoromethyl-2-aminophenylthio) benzonitrile

HRID 1082065Notes

Reaction equation

HRID 1082065 reaction equation
[CH:1]1[C:6]2[C:7](=S)[NH:8]C3C=CC=CC=3S[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[C:22]([NH2:27])[CH:21]=1.FC1C=CC=CC=1C#N>CN(C=O)C>[F:29][C:19]([F:18])([F:28])[C:20]1[CH:25]=[CH:24][C:23]([S:26][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:6]=2[C:7]#[N:8])=[C:22]([NH2:27])[CH:21]=1

Participants

5

Reactant 3

HCID 678552-FluorobenzonitrileHCID 667552Dibenzo[b,f][1,4]thiazepine-11(10H)-thioneHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochloride

Product 1

HCID 105418032-(4-Trifluoromethyl-2-aminophenylthio) benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a procedure analagous to that of Example 3(a) and (b), 4-trifluoromethyl-2-aminothiophenol hydrochloride (11.48 g, 50 mmol) was combined with 2-fluorobenzonitrile in DMF solvent (100 ml) to give crude 2-(4-trifluoromethyl-2-aminophenylthio) benzonitrile (6.84 g). Hydrolysis and subsequent condensation gave the title compound as off-white crystals from ethanol (1.1 g, m.p. 233°-235° C., Rf 0.21, CH2Cl2 /MeOH 50:1).

Sources & evidence

ORD record
ord-ef0b26c4f28f45f1ab0a5bcdc64bfc98
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

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