Triethylamine → HCID 23085229, compound

HRID 1442573Notes

Reaction equation

HRID 1442573 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:18](OC)(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[SH:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:26]=[C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:1]([C:3]2[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 23085230HCID 23085230, compound

Product 1

HCID 23085229HCID 23085229, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl 3-(3-cyanophenyl)propionate (0.74 g, 3.2 mmol), methyl thiosalicylate (1.1 g, 6.4 mmol), triethylamine (0.67 ml, 4.8 mmol) and toluene (3 ml) was heated and refluxed for 27 hours under a nitrogen flow. The reaction mixture was applied to column chromatography using silica gel (50 g). Fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give the title compound (0.19 g, 16%) as crystals.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 27 hours under a nitrogen flow
  3. washFractions eluted with hexane-ethyl acetate (2:1
  4. customv/v) were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72bc15bfcf27404ba5d76928189697f1
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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