Potassium Hydroxide → HCID 19768570, compound

HRID 1590905Notes

Reaction equation

HRID 1590905 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[S:6].[N+:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[C-:13].[OH-].[K+]>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[S:6][CH:13]=[N:12][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 533707Ethyl isocyanoacetateHCID 19768519HCID 19768519, compound

Product 1

HCID 19768570HCID 19768570, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to the method described in Synthesis 10, (1976), 681-682, 47 g (169 mmol) of O-methyl 3-iodothiobenzoate were reacted with ethyl isocyanoacetate in the presence of 1-5% powdered potassium hydroxide in ethanol. Recrystallization from ether yielded 45.8 g (75.4%) of ethyl 5-(3-iodophenyl)-4-thiazolecarboxylate as ochre crystals, melting point 77°-78°.

Workup

  1. customRecrystallization from ether

Sources & evidence

ORD record
ord-d1a6e7092eba4142bab68a10eb799c18
Source dataset
uspto-grants-1993_04
Patent number
US05204482

Reaction notes

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