Triethylamine → HCID 178527819, compound

HRID 1064869Notes

Reaction equation

HRID 1064869 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](Cl)(Cl)=[S:10].C(N(CC)CC)C>C1COCC1>[SH:10][C:9]1[NH:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][CH:6]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99562,3-DiaminopyridineHCID 10040Thiophosgene

Product 1

HCID 178527819HCID 178527819, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-diaminopyridine (286 mg, 2.62 mmol) in THF (10 ml) were added thiophosgene (300 mg, 2.62 mmol) and triethylamine (265 mg, 2.62 mmol), and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated in vacuo, and the resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1) to provide 39 mg (yield 10%) of 2-mercaptoimidazolo[4,5-b]pyridine.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1)

Sources & evidence

ORD record
ord-95f39c5a5e264f8781273bee9a82da30
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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