Triethylamine → HCID 59750272, compound

HRID 748472Notes

Reaction equation

HRID 748472 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=1)(=[O:3])[CH3:2].[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>C1(C)C=CC=CC=1>[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17](=[O:25])[N:16]=2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939269HCID 22939269, compound

Product 1

HCID 59750272HCID 59750272, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(1-Acetyl-2-pyrrolidinyl)-2-pyridinecarbonitrile (0.32 g, 1.5 mmol) and methyl thiosalicylate (1.02 g, 6.0 mmol) were dissolved in toluene (4 ml), and triethylamine (2.0 ml, 14.3 mmol) was added thereto. The mixture was refluxed for 24 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (8:1, v/v) were collected, concentrated and recrystallized from diethyl ether-methanol to give the titled compound (0.25 g, 48%) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 24 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate-methanol (8:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from diethyl ether-methanol

Sources & evidence

ORD record
ord-1b4fd0ea39f344f5a205046dbd243509
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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