Toluene → HCID 58610116, compound

HRID 1442597Notes

Reaction equation

HRID 1442597 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:16](OC)(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[SH:19].C(N(CC)CC)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH2:12]([N:9]([CH2:10][CH3:11])[C:7](=[O:8])[C:6]1[CH:14]=[CH:15][C:3]([C:1]2[S:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[C:16](=[O:24])[N:2]=2)=[CH:4][CH:5]=1)[CH3:13]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 14982027HCID 14982027, compound

Product 1

HCID 58610116HCID 58610116, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-cyano-N,N-diethylbenzamide (0.60 g, 3.0 mmol), methyl thiosalicylate (0.75 g, 4.5 mmol), triethylamine (0.54 g, 5.3 mmol) and toluene (5 ml) was heated and refluxed under a nitrogen flow for 70 hours. To the reaction solution, ethyl acetate was added and the solid precipitated was removed by filtration. After the filtrate was ice-cooled, the crystals precipitated were taken by filtration and recrystallized from ethyl acetate to give the title compound (0.31 g, 30%) as crystals.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed under a nitrogen flow for 70 hours
  3. customthe solid precipitated
  4. customwas removed by filtration
  5. temperaturecooled
  6. customthe crystals precipitated
  7. filtrationwere taken by filtration
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4d1b4d3d149c411b89ff3b555301c88c
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

Loading…