Triethylamine → HCID 58610105, compound

HRID 1442604Notes

Reaction equation

HRID 1442604 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([NH:13][CH2:14][CH3:15])[CH:4]=1)#[N:2].[C:16](OC)(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[SH:19].C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[CH2:14]([NH:13][C:5]1[CH:4]=[C:3]([C:1]2[S:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[C:16](=[O:24])[N:2]=2)[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 23076867Methyl 4-cyano-2-(ethylamino)benzoate

Product 1

HCID 58610105HCID 58610105, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of methyl 4-cyano-2-(ethylamino)benzoate (1.23 g, 6.02 mmol), methyl thiosalicylate (1.52 g, 9.04 mmol), triethylamine (1.7 mL, 12 mmol) and xylene (6 mL) was stirred at 145° C. for 18 hours under a nitrogen flow. After the reaction mixture was allowed to cool, the crystals were taken by filtration and recrystallized from methanol to give the title compound (450 mg, 22%).

Workup

  1. temperatureto cool
  2. filtrationthe crystals were taken by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2f976b757e5b42358e5f2f7ca86d0cf6
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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