Triethylamine → HCID 58610099, compound

HRID 1442591Notes

Reaction equation

HRID 1442591 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[C:13](OC)(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[SH:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([C:7]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:13](=[O:21])[N:8]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 67995Benzonitrile, 4-(trifluoromethyl)-

Product 1

HCID 58610099HCID 58610099, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-trifluoromethylbenzonitrile (2.00 g, 12 mmol), methyl thiosalicylate (3.93 g, 23 mmol), triethylamine (2.40 g, 24 mmol) and toluene (10 ml) was heated and refluxed for 25 hours under a nitrogen flow. The reaction solution was concentrated under reduced pressure and the residue was applied to column chromatography using silica gel (100 g). Fractions eluted with hexane-ethyl acetate (5:1, v/v) were concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to give the title compound (0.58 g, 16%) as crystals.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 25 hours under a nitrogen flow
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washFractions eluted with hexane-ethyl acetate (5:1
  5. concentrationv/v) were concentrated under reduced pressure
  6. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-de6e1bc92ae445ffb281b11188cd7f3b
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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