Potassium Hydroxide → N-(2-Ethoxyethyl)-4-methoxy-2-methylthiophen-3-amine

HRID 978927Notes

Reaction equation

HRID 978927 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH3:15][O:16][C:17]1[C:18]([NH:23][C:24](=O)[CH2:25][O:26][CH2:27][CH3:28])=[C:19]([CH3:22])[S:20][CH:21]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH2:27]([O:26][CH2:25][CH2:24][NH:23][C:18]1[C:17]([O:16][CH3:15])=[CH:21][S:20][C:19]=1[CH3:22])[CH3:28]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 202010992-Ethoxy-N-(4-methoxy-2-methylthiophen-3-yl)acetamideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 20201091N-(2-Ethoxyethyl)-4-methoxy-2-methylthiophen-3-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 70 ml (0.245 mol) of sodium bis(2-methoxyethoxy)aluminium hydride (70% solution in toluene) and 30 ml of dry toluene is added dropwise with stirring a solution of 9.4 g (0.041 mol) of N-(4-methoxy-2-methyl-thien-3-yl)-ethoxyacetamide in 125 ml of dry toluene. After the exothermic reaction has subsided, stirring is continued for a further 90 minutes and the reaction solution then cautiously added in small portions at -10° to 100 ml of 20% KOH solution.

Workup

  1. customAfter the exothermic reaction

Sources & evidence

ORD record
ord-0920b7230dd747e2b8071ab3bf36413c
Source dataset
uspto-grants-1987_05
Patent number
US04666502

Reaction notes

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