Triethylamine → HCID 59750272, compound

HRID 499652Notes

Reaction equation

HRID 499652 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-5a868e33be214360baf598d277d5de7b
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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