Methyl cyanoacetate → HCID 19041044, compound

HRID 1683798Notes

Reaction equation

HRID 1683798 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N+:19]=3[O-])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])#[N:26]>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:27]([C:28]([O:30][CH3:31])=[O:29])[C:25]#[N:26])[N:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 7747Methyl cyanoacetateHCID 19041120HCID 19041120, compound

Product 1

HCID 19041044HCID 19041044, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3 g of 2-[2-(3,4-diethoxyphenyl)-4-thiazolyl]pyridine-1-oxide, 2.6 g of methyl cyanoacetate and 150 ml of acetic anhydride was stirred at 110° C. for 4 hours and then allowed to cool. The resulting crystals were collected by filtration and recrystallized from ethanol-dimethylformamide to obtain 2.1 g of 2-(3,4-diethoxyphenyl)-4-[6-(1-methoxycarbonyl-1-cyanomethyl)-2-pyridyl]thiazole.

Workup

  1. temperatureto cool
  2. filtrationThe resulting crystals were collected by filtration
  3. customrecrystallized from ethanol-dimethylformamide

Sources & evidence

ORD record
ord-5a5b9f4cc2704f3a9e8bbd57e371a208
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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