Sulfuryl chloride → 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one

HRID 577601Notes

Reaction equation

HRID 577601 reaction equation
[NH2:1][C:2]1[C:11]([I:12])=[C:10]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][C:14]=2[CH3:19])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:20].S(Cl)([Cl:24])(=O)=O>C(O)(=O)C>[NH2:1][C:2]1[C:11]([I:12])=[C:10]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][C:14]=2[CH3:19])[C:9]([Cl:24])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:20]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 867238275-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 867238285-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-oneYield 202.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Two batches of 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one (293e, 2.5 g/6.5 mmol each batch, 5.0 g/13 mmol total) in glacial acetic acid (100 mL each batch) were treated with sulfuryl chloride (1 g, 75 mmol each batch), added dropwise at 20-25° C. The mixtures were stirred for 2 hours, then combined and concentrated under vacuum to remove volatiles. The residue was purified by silica gel chromatography (10:1 dichloromethane/methanol) to give 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one (293f, 5.5 g, 90% purity, 90% yield) as a yellow solid.

Workup

  1. additionadded dropwise at 20-25° C
  2. concentrationconcentrated under vacuum
  3. customto remove volatiles
  4. customThe residue was purified by silica gel chromatography (10:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-d2d3b44f550e4c5a8d19b4ffb882cceb
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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