Thionyl Chloride → Thieno[2,3-b]pyrazine-6-carbonyl chloride

HRID 1184873Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:2]=12.S(Cl)([Cl:15])=O>>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10]([Cl:15])=[O:12])=[CH:9][C:2]=12

Participants

Reactant 2

HCID 24386Thionyl Chloride

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

Product 1

HCID 86680174Thieno[2,3-b]pyrazine-6-carbonyl chlorideYield 100%

Procedure

A solution of thieno[2,3-b]pyrazine-6-carboxylic acid (400 mg, 2.220 mmol) in thionyl chloride (1.6 mL, 22.20 mmol) was heated to 80° C. for 2 h. Concentrated to dryness and coevaporated with toluene to give thieno[2,3-b]pyrazine-6-carbonyl chloride 63 (441 mg, 100%).

Workup

concentrationConcentrated to dryness

Sources & evidence

ORD record: ord-9f22d6a82e7842899db951deb787e8c2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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