Heptanenitrile, 7-bromo- → HCID 22246898, compound

HRID 2298127Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[CH2:11][NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25]>>[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:12]([CH2:11]/[CH:10]=[CH:9]/[C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[S:13]([CH3:16])(=[O:15])=[O:14])#[N:25]

Participants

Reactant 2

HCID 88737Heptanenitrile, 7-bromo-

HCID 22246824HCID 22246824, compound

Product 1

HCID 22246898HCID 22246898, compoundYield 79.7%

Procedure

In an analogous manner to the procedure described in Step A of Example 1, trans-N-[3-(3,5-dichloro-phenyl)-allyl]-methanesulfonamide (500 mg, 2.45 mmol) was alkylated with 7-bromoheptanenitrile (781 mg, 2.94 mmol) at room temperature over 24 h to provide the title compound of Step A (760 mg). 1H NMR (CDCl3 400 MHz) δ 7.26 (m, 3H), 6.49 (d, 1H), 6.22 (m, 1H), 3.98 (m, 2H), 3.22 (t, 2H), 2.88 (s, 3H), 2.36 (t, 2H), 1.68-1.35 (m, 8H).

Sources & evidence

ORD record: ord-d432e12b88794885945f0ddaf89b309e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492412B2

Reaction notes

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