Ethanol → Ethyl thieno[2,3-b]pyrazine-6-carboxylate

HRID 1184858Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:2]=12.OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH2:24](O)[CH3:25]>>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10]([O:12][CH2:24][CH3:25])=[O:11])=[CH:9][C:2]=12

Participants

Reactant 4

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 10340Sodium Carbonate

HCID 7164578Thieno[2,3-b]pyrazine-6-carboxylic acid

Product 1

HCID 12299125Ethyl thieno[2,3-b]pyrazine-6-carboxylateYield 80%

Conditions

Temperature: 80 °C

Procedure

Thieno[3,2-b]pyrazine-6-carboxylic acid (2 g, 11.10 mmol) was dissolved in ethanol (30 mL). Concentrate H2SO4 (5.92 mL, 111 mmol) was slowly added. The resulting mixture was heated at 80° C. overnight. The reaction mixture was cooled en neutralized with saturated Na2CO3 solution. The resulting precipitate was collected to give ethyl thieno[3,2-b]pyrazine-6-carboxylate 86 (1.85 g, 80%) as a brown solid. (m/z)=209 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
customThe resulting precipitate was collected

Sources & evidence

ORD record: ord-1a170fe38cc94ee5b3b9fc34d5c35f85
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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