Dimethylformamide → 1-Chloroisoquinoline-5-sulfonyl chloride

HRID 1067239Notes

Reaction equation

HRID 1067239 reaction equation
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([OH:15])(=O)=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.CN(C=O)C.S(Cl)([Cl:23])=O>>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([S:12]([Cl:23])(=[O:15])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 137300201-Chloroisoquinoline-5-sulfonic acid

Product 1

HCID 219797811-Chloroisoquinoline-5-sulfonyl chloride

Procedure

A suspension of 1-chloro-5-isoquinolinesulphonic acid (1.14 g, 4.68 mmol) in thionyl chloride (13 mL) and DMF (0.3 mL, 3.9 mmol) was heated to reflux for 3 h. Concentration in vacuo and azeotroping with toluene gave 1-chloro-5-chlorosulphonylisoquinoline as an off-white solid which was used immediately.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationConcentration in vacuo
  4. customazeotroping with toluene

Sources & evidence

ORD record
ord-f43a5f12e3d040d1bd5f309686b170a0
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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