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Dimethylformamide → N-(2-chloro-4-cyanophenyl)methanesulfonamide

HRID 1350833
Notes
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Reaction equation

HRID 1350833 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 11681502N-(2-Chloro-4-iodophenyl)methanesulfonamide

Product 1

HCID 11615562N-(2-chloro-4-cyanophenyl)methanesulfonamideYield 88%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

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

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationThen, filtration, evaporation
  4. customto remove solvent
  5. customgave the crude residue, which
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes