3,4-Diethoxybenzene-1-carbothioamide → HCID 19041124, compound

HRID 1683778Notes

Reaction equation

HRID 1683778 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([NH2:9])=[S:8])[CH3:2].[CH2:16]([O:18][C:19]([C:21]1[C:26]([OH:27])=[CH:25][CH:24]=[C:23]([C:28](=O)[CH2:29]Br)[N:22]=1)=[O:20])[CH3:17]>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[S:8][CH:29]=[C:28]([C:23]3[CH:24]=[CH:25][C:26]([OH:27])=[C:21]([C:19]([O:18][CH2:16][CH3:17])=[O:20])[N:22]=3)[N:9]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]

Participants

4

Reactant 2

HCID 77452503,4-Diethoxybenzene-1-carbothioamideHCID 15541470HCID 15541470, compound

Product 1

HCID 19041124HCID 19041124, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.7 g of 3,4-diethoxythiobenzamide and 20 ml of ethanol were added to 0.77 g of 2-ethoxycarbonyl-3-hydroxy-6-(2-bromoacetyl)pyridine. The mixture was refluxed for 3 hours. Ethanol was removed by distillation. To the residue was added ethyl acetate-dichloromethane to give rise to crystallization to obtain 0.62 g of 2-(3,4-diethoxyphenyl)-4-(5-hydroxy-6-ethoxycarbonyl-2-pyridyl)thiazole.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customEthanol was removed by distillation
  3. additionTo the residue was added ethyl acetate-dichloromethane
  4. customto give rise
  5. customto crystallization

Sources & evidence

ORD record
ord-c928b5dd04f04038915d5140e765530e
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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