Dimethylformamide → HCID 11615562, compound

HRID 1350833Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH3:14][N:15](C)C=O>C(OCC)(=O)C.C1(C)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([C:14]#[N:15])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of N-(2-chloro-4-iodophenyl)methanesulfonamide (4.4 g, 13.3 mmol, Industrie Chimique Belge 1974, 39, 490–500), zinc(II)cyanide (1.95 g, 16.6 mmol) and palladium(0) tetrakis(triphenyl phosphine) (1.53 g, 1.33 mmol) in N,N-dimethyl formamide (DMF) (30 ml) was heated at 90° C. for 1.5 hours. Then, the mixture was diluted with ethyl acetate and toluene (8:1) solution (250 ml) and washed with water, brine, dried over sodium sulfate. Then, filtration, evaporation to remove solvent gave the crude residue, which was applied to a silica gel chromatography column and eluted with a volume mixture of methylene dichloride/hexane(2/1 to 4/2) to furnish 2.69 g (88% yield) of title compound as a white solid.

Workup

washwashed with water, brine
dry with materialdried over sodium sulfate
filtrationThen, filtration, evaporation
customto remove solvent
customgave the crude residue, which
washeluted with a volume mixture of methylene dichloride/hexane(2/1 to 4/2)

Sources & evidence

ORD record: ord-e1d3ee0aaa5f46e3a6955b05c88d8e2b
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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