Dichlorodimethylsilane → 7-Mercapto-3,4-dihydro-2H-isoquinolin-1-one

HRID 1364189Notes

Reaction equation

HRID 1364189 reaction equation
Cl[Si](Cl)(C)C.[O:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:17](Cl)(=O)=O)[CH:15]=2)[CH2:10][CH2:9][NH:8]1.CN1CCN(C)C1=O>ClCCCl.[Zn]>[SH:17][C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH2:9][NH:8][C:7]2=[O:6])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 180713741-Oxo-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Product 1

HCID 642254267-Mercapto-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To a zinc powder (2.79 g, 42.7 mmol) and Dichlorodimethylsilane (5.15 mL, 42.7 mmol) in DCE (45 mL) is added a solution of 1-Oxo-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (3 g, 12.2 mmol) and 1,3-dimethylimidazolidin-2-one (3.96 mL, 36.6 mmol) in DCE (5 mL). After stirring at rt during 2 h, the mixture is concentrated.

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-0333231d9de44f7b930d83cd99972a19
Source dataset
uspto-grants-2011_02
Patent number
US07888351B2

Reaction notes

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