Triethylamine → HCID 59750231, compound

HRID 748121Notes

Reaction equation

HRID 748121 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH2:12]([N:19]([C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[N:28]=1)=[O:26])[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([N:19]([C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:34]=2)[N:28]=1)=[O:26])[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 68455640HCID 68455640, compound

Product 1

HCID 59750231HCID 59750231, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.8 g, 10.7 mmol), N-benzyl-N-[(6-cyano-2-pyridyl)carbonyl]-N′,N′-dimethylurea (1.6 g, 5.4 mmol), triethylamine (2.0 ml, 14 mmol) and toluene (4 ml) was refluxed for 8 hrs as described in Example 1. After cooling, the precipitated crystals were collected by filtration and recrystallized from hexane-chlorobenzene to give the titled compound (2.2 g, 93%) as crystals.

Workup

  1. temperaturewas refluxed for 8 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from hexane-chlorobenzene

Sources & evidence

ORD record
ord-a31e3793de6d42a2b9f927931c08fbdf
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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