Diisopropyl Ether → HCID 59750460, compound

HRID 499611Notes

Reaction equation

HRID 499611 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][N:4]=1)#[N:2].[C:17](OC)(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[SH:20].C(N(CC)CC)C.C(OC(C)C)(C)C>C1(C)C=CC=CC=1>[CH3:16][CH:10]([CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17](=[O:25])[N:2]=2)[CH:8]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939428HCID 22939428, compound

Product 1

HCID 59750460HCID 59750460, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 3-(2-cyano-4-pyridyl)-2-methylpropionate (0.50 g, 2.3 mmol) and methyl thiosalicylate (0.96 g, 5.7 mmol) were dissolved in toluene (2 ml), and triethylamine (1.0 ml, 5.7 mmol) was added thereto. The reaction mixture was refluxed for 8 hrs and combined with isopropyl ether to precipitate crystals, which were collected by filtration and recrystallized from ethyl acetate to give the titled compound (0.43 g, 53%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hrs
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d06fce8d35dc4e5aafb3042bf3a0469a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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