Sodium hydride → 3-Bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine

HRID 1774772Notes

Reaction equation

[S:1]1(=[O:7])(=[O:6])[CH2:5][CH2:4][CH2:3][NH:2]1.[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:15]Cl)[CH:14]=1.[H-].[Na+]>>[Br:8][C:9]1[CH:14]=[C:13]([CH2:15][N:2]2[CH2:3][CH2:4][CH2:5][S:1]2(=[O:7])=[O:6])[CH:12]=[N:11][CH:10]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 6421571,3-Propanesultam

HCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 595783953-Bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine

Procedure

In analogy to the procedure described for the preparation of intermediate A-12 [B], isothiazolidine 1,1-dioxide was reacted with 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A]) in the presence of NaH to give the title compound as a light yellow oil. MS: 292.8 and 290.9 (M+H+).

Sources & evidence

ORD record: ord-05f2883d30dd4c49a374010e31832bce
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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