Sodium hydride → 4-[3-(6-Bromopyridin-3-yl)propyl]thiomorpholin-3-one

HRID 1896698Notes

Reaction equation

HRID 1896698 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][S:6][CH2:5][C:4]1=[O:9].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19]Br)=[CH:13][N:12]=1>CN(C=O)C>[Br:10][C:11]1[N:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][N:3]2[CH2:8][CH2:7][S:6][CH2:5][C:4]2=[O:9])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 884021,4-Tetrahydrothiazine-3-oneHCID 714277712-Bromo-5-(3-bromopropyl)pyridine

Product 1

HCID 714277704-[3-(6-Bromopyridin-3-yl)propyl]thiomorpholin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60.2 mg (1.38 mmol) of sodium hydride (55% suspension in mineral oil) were added to 161.7 mg (1.38 mmol) of thiomorpholin-3-one in 5 ml of DMF, and the mixture was stirred at room temperature for 15 min. Subsequently, 350 mg (1.25 mmol) of 2-bromo-5-(3-bromopropyl)pyridine were added. The reaction mixture was stirred for 3.5 h, concentrated, admixed with water and extracted with ethyl acetate. The organic phase was separated and concentrated. Yield: 421 mg.

Workup

  1. stirringThe reaction mixture was stirred for 3.5 h
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3a1979e7db34a9cbabcf372a0f085e5
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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