Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochloride → HCID 21463522, compound

HRID 1940607Notes

Reaction equation

HRID 1940607 reaction equation
Cl.[NH2:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:4]=1[SH:12].[C:13]([CH2:15][CH2:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])#N>ClC1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[F:9][C:8]1[C:3]2[N:2]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[S:12][C:4]=2[C:5]([F:11])=[CH:6][C:7]=1[F:10]

Participants

5

Reactant 2

HCID 11390282Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochlorideHCID 11849916HCID 11849916, compound

Product 1

HCID 21463522HCID 21463522, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7964ChlorobenzeneSolvent3×

Procedure

To a solution of zinc chloride (26 mg, 0.19 mmol) in chlorobenzene (3 ml) was added a solution of 2-amino-3,4,6-trifluorothiophenol hydrochloride (269 mg, 1.2 mmol) in chlorobenzene (1 ml) and a solution of ethyl 3-(2-cyanoethyl)benzoate (254 mg, 1.2 mmol) in chlorobenzene (1 ml) and the mixture was heated to reflux for 40 hours. The reaction mixture was evaporated followed by addition of methylene chloride. The resulting mixture was washed with water, dried and evaporated to yield a residue, which was purified on a silica gel column to give ethyl 3-[2-(4,5,7-trifluorobenzothiazol-2-yl)ethyl]benzoate (133 mg, 30%) as an oil.

Workup

  1. temperatureto reflux for 40 hours
  2. customThe reaction mixture was evaporated
  3. additionfollowed by addition of methylene chloride
  4. washThe resulting mixture was washed with water
  5. customdried
  6. customevaporated
  7. customto yield a residue, which
  8. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-1cfd1f810a014e9980e1501e539a0341
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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