O-Xylene → HCID 54536413, compound

HRID 1940625Notes

Reaction equation

HRID 1940625 reaction equation
C1(C)C(C)=CC=CC=1.Cl.[NH2:10][C:11]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[C:13]([F:19])[C:12]=1[SH:20].[CH2:21]([O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]#N)[CH3:22]>C(O)C>[CH2:21]([O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[S:20][C:12]2[C:13]([F:19])=[CH:14][C:15]([F:18])=[C:16]([F:17])[C:11]=2[N:10]=1)[CH3:22]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 24976Hexanoic acid, 6-cyano-, ethyl esterHCID 11390282Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochloride

Product 1

HCID 54536413HCID 54536413, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To xylene (6 ml) was added 2-amino-3,4,6-trifluorothiophenol hydrochloride (647 mg, 3 mmol), 6-cyanohexanoic acid ethyl ester (507 mg, 3 mmol) and ethanol (0.5 ml) and the mixture was heated to reflux for 60 hours under a nitrogen stream. The resultant reaction mixture was washed with water, dried and then evaporated to yield a residue, which was purified on a silica gel column to give 6-(4,5,7-trifluorobenzothiazol-2-yl)hexanoic acid ethyl ester (395 mg, 40%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 60 hours under a nitrogen stream
  3. customThe resultant reaction mixture
  4. washwas 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-a641376a0374424086cbe4cf57ea4219
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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