Allyl bromide → HCID 22988177, compound

HRID 987004Notes

Reaction equation

HRID 987004 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH2:14][NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[S:17])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[CH2:25](Br)[CH:26]=[CH2:27]>O1CCCC1>[CH2:27]([S:17][C:16](=[N:15][CH2:14][C:5]1[C:4]([Cl:3])=[CH:9][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:7][N:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 22629936HCID 22629936, compound

Product 1

HCID 22988177HCID 22988177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of sodium hydride (0.33 g) in tetrahydrofuran (10 ml) was added N-[(3-chloro-5-trifluoromethyl-2-pyridyl)methyl]-2-chlorobenzenethioamide (for preparation see PCT/GB/99/00304) (3.07 g) in tetrahydrofuran (50 ml) dropwise with stirring for 20 minutes until effervescence had ceased. Allyl bromide (0.09 g) in tetrahydrofuran (5 ml) was added to the reaction mixture, and the solution was stirred overnight at room temperature. The mixture was evaporated to dryness and the residue partitioned between dichloromethane (10 ml), water (5 ml) and brine (5 ml). The organic phase was separated and the solvent and any residual water evaporated in vacuo. The residue was purified by silica gel chromatography, gradient eluting with light petroleum (b.p. 60-80° C.)/diethyl ether to give the title product.

Workup

  1. stirringthe solution was stirred overnight at room temperature
  2. customThe mixture was evaporated to dryness
  3. customthe residue partitioned between dichloromethane (10 ml), water (5 ml) and brine (5 ml)
  4. customThe organic phase was separated
  5. customthe solvent and any residual water evaporated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washgradient eluting with light petroleum (b.p. 60-80° C.)/diethyl ether

Sources & evidence

ORD record
ord-58b1e674abdd4bcdad2b8b82430e705d
Source dataset
uspto-grants-2003_10
Patent number
US06630495B1

Reaction notes

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