Dimethylformamide → Isoquinoline-5-sulfonyl chloride hydrochloride

HRID 2219190Notes

Reaction equation

HRID 2219190 reaction equation
CN(C=O)C.[CH:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([OH:19])(=O)=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1.S(Cl)([Cl:22])=O>C(Cl)Cl>[ClH:22].[CH:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([Cl:22])(=[O:19])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 2415995-Isoquinolinesulfonic acid

Product 1

HCID 13116932Isoquinoline-5-sulfonyl chloride hydrochlorideYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous DMF (1.5 mL) is added dropwise to a stirred suspension of isoquinoline-5-sulfonic acid (28.3 g, 135 mmol) in thionyl chloride (150 mL, 2.06 mole) at ambient temperature under nitrogen. The resultant mixture is heated to reflux for 2.5 hours. After being cooled to ambient temperature, the mixture is concentrated under vacuum to give a yellowish powder. The powder is suspended in dry CH2Cl2 (200 mL), sonicated, filtered and dried at 40° C. under vacuum to give 29.2 g (111 mmol, 82% yield) of the title compound. 1H NMR (TFA-d1): δ8.48 (t, J=7.9 Hz, 1H), 9.13-9.14 (m, 2H), 9.29 (d, J=7.9 Hz, 1H), 9.57 (d, J=7.0 Hz, 1H), 10.26 (s, 1H).

Workup

  1. temperatureto reflux for 2.5 hours
  2. concentrationthe mixture is concentrated under vacuum
  3. customto give a yellowish powder
  4. customsonicated
  5. filtrationfiltered
  6. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-85cbcf8cdd3048dbb0276d52bf48af46
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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