Sodium Azide → 4-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane

HRID 2354502Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[CH:10](OS(C)(=O)=O)[CH3:11])=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O.C(OC(C)C)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[CH:10]([N:25]=[N+:26]=[N-:27])[CH3:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-methylsulfonyloxybutane (1.1 kg, 2.9 mol) in N,N-dimethylformamide (4.1 L) was added sodium azide (378 g, 5.8 mol), and the reaction was heated at 70° C. for 7 h. After cooling to room temperature, the reaction mixture was diluted with isopropyl acetate (11 L) and was washed with sodium bicarbonate (50% saturated aqueous solution) and water (5.5 L). The organic layer was separated and treated with Darco KB (254 g) overnight. The mixture was filtered over solka floc, washed with toluene and concentrated. The residue was diluted with toluene (1 L) and was loaded onto a silica gel pad, which was eluted with 90:10 hexane/ethyl acetate to give the title compound.

Workup

temperatureAfter cooling to room temperature
washwas washed with sodium bicarbonate (50% saturated aqueous solution) and water (5.5 L)
customThe organic layer was separated
additiontreated with Darco KB (254 g) overnight
filtrationThe mixture was filtered over solka floc
washwashed with toluene
concentrationconcentrated
additionThe residue was diluted with toluene (1 L)
washwas eluted with 90:10 hexane/ethyl acetate

Sources & evidence

ORD record: ord-ae17286e2304478b8170f91b408dc184
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754188B2

Reaction notes

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