Ethyl Thioglycolate → HCID 178473139, compound

HRID 1095455Notes

Reaction equation

HRID 1095455 reaction equation
O[C:2]1([C:14]2[NH:15][CH:16]=[N:17][CH:18]=2)[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]#[N:13])[CH:5]=[CH:4][C:3]1=2.[SH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:12]([C:6]1[CH:7]=[C:8]2[C:3](=[CH:4][CH:5]=1)[C:2]([S:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])([C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)[CH2:11][CH2:10][CH2:9]2)#[N:13]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 14798Sodium HydroxideHCID 667822465-hydroxy-5-(3H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 178473139HCID 178473139, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.00 mmol of 5-hydroxy-5-(3H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (Example 2c1) and 10 mmol of ethyl mercaptoacetate [623-51-8] in 2 ml of trifluoroacetic acid is stirred at 70° C. for 24 hours. The reaction mixture is cooled to room temperature, poured into ice-water and neutralized with 4M sodium hydroxide solution. The mixture is extracted with ethyl acetate, and the combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. dry with materialthe combined organic phases are dried with sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-4cc276b10fba48cfa6699d6d765e9e48
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

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