Sodium hydride → HCID 53700730, compound

HRID 2111609Notes

Reaction equation

HRID 2111609 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Cl.[CH2:14]([N:21]([CH2:25][CH2:26]Cl)[CH2:22][CH2:23]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1.CS(C)=O>[CH2:14]([N:21]1[CH2:25][CH2:26][C:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)([C:11]#[N:12])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanideHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

Product 1

HCID 53700730HCID 53700730, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 9.8 g of 60% sodium hydride in oil in 140 ml of THF and 60 ml of DMSO is added dropwise, at rt, a solution of 11.3 g of 4-chlorophenylacetonitrile and 20 g of benzyl[bis(2-chloroethyl)]amine hydrochloride in 140 ml of THF and 60 ml of DMSO, and the mixture is then heated at 70-80° C. for 2 hours. After cooling, the reaction mixture is poured onto ice and extracted with ether, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a heptane/EtOAc mixture (90/10; v/v). 19.6 g of the expected compound are obtained.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured onto ice
  3. extractionextracted with ether
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a heptane/EtOAc mixture (90/10; v/v)

Sources & evidence

ORD record
ord-cb74cddf5d634e1ca3d67c6eed2ac938
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

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