Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochloride → HCID 21463504, compound

HRID 1940633Notes

Reaction equation

HRID 1940633 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][C:12]#[N:13])[CH:5]=1)#[N:2].Cl.N[C:16]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[C:18]([F:24])[C:17]=1[SH:25]>C(O)C>[F:22][C:21]1[C:16]2[N:13]=[C:12]([CH2:11][C:6]3[CH:5]=[C:4]([CH2:3][C:1]#[N:2])[CH:9]=[C:8]([CH3:10])[CH:7]=3)[S:25][C:17]=2[C:18]([F:24])=[CH:19][C:20]=1[F:23]

Participants

4

Reactant 2

HCID 11390282Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochlorideHCID 193493962,2'-(5-Methyl-1,3-phenylene)diacetonitrile

Product 1

HCID 21463504HCID 21463504, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,3-biscyanomethyl-5-methylbenzene (2.89 g, 17 mmol) and 2-amino-3,4,6-trifluorothiophenol hydrochloride (3.66 g, 17 mmol) in absolute ethanol was heated at 170° C. for 15 hours under a nitrogen stream in an autoclave. After the reaction, evaporation of the solvent left a residue, which was purified on a silica gel column and recrystallized from ethyl acetate-hexane to obtain 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]-5-methylphenylacetonitrile (1.86 g, 33%).

Workup

  1. customAfter the reaction, evaporation of the solvent
  2. waitleft a residue, which
  3. customwas purified on a silica gel column
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1432fb332a554014879cd96ecb55d5ee
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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