Sodium Iodide → HCID 53970490, compound

HRID 1683124Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[I-].[Na+].[H-].[Na+].Cl.Cl[CH2:17][CH2:18][N:19]([CH2:27][CH2:28]Cl)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([N:19]1[CH2:27][CH2:28][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)([C:9]#[N:10])[CH2:17][CH2:18]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Methylphenyl-acetonitrile (1.66 g, 12.6 mmol), sodium iodide (0.25 g), and sodium hydride (50.4 mmol) were combined in dimethylformamide (50 mL) and stirred until gas evolution ceases. A solution of N,N-bis(2-chloroethyl)-N-benzylamine hydrochloride (2.8 g, 12.6 mmol) in dimethylformamide (50 mL) was added dropwise. After 24 hours, the reaction mixture was heated to 70° C. and stirred for 2 days. The solvent was removed by evaporation in vacuo to give a residue and the residue was partitioned between water and dichloromethane. The organic layer was separated, dried over MgSO4, filtered and evaporated in vacuo to give a residue which was chromatographed on silica gel eluting with 2/1 hexane/ethyl acetate to give the title compound.

Workup

stirringstirred for 2 days
customThe solvent was removed by evaporation in vacuo
customto give a residue
customthe residue was partitioned between water and dichloromethane
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
customevaporated in vacuo
customto give a residue which
customwas chromatographed on silica gel eluting with 2/1 hexane/ethyl acetate

Sources & evidence

ORD record: ord-0e4e7c660a7841109b04b9a666599979
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05635510

Reaction notes

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