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

HRID 1184901Notes

Reaction equation

HRID 1184901 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:5]2=[N:4][CH:3]=1.S(Cl)([Cl:16])=O>>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([Cl:16])=[O:13])=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 823939523-Chlorothieno[2,3-b]pyrazine-6-carboxylic acid

Product 1

HCID 866801793-Chlorothieno[2,3-b]pyrazine-6-carbonyl chlorideYield 100%

Procedure

A solution of 3-chlorothieno[2,3-b]pyrazine-6-carboxylic acid 93 (0.191 mmol, 41 mg) in thionyl chloride (27.4 mmol, 2 ml, 3262 mg) was heated at 80° C. for 2 h. Reaction mixture was concentrated under reduced pressure and co-evaporated with toluene (2×) to give 3-chlorothieno[2,3-b]pyrazine-6-carbonyl chloride 94 (44 mg, 100%).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure and co-evaporated with toluene (2×)

Sources & evidence

ORD record
ord-9d4a549b44844e288cb96bda05fd7e51
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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