2-Chloro-4-iodoaniline → HCID 22707299, compound

HRID 2305335Notes

Reaction equation

HRID 2305335 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C([N-]C(C)C)(C)C.[Li+].[CH3:18][N:19]([CH3:33])[S:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[C:25](F)[CH:24]=1)(=[O:22])=[O:21]>O1CCCC1>[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:25]1[CH:24]=[C:23]([S:20](=[O:22])(=[O:21])[N:19]([CH3:18])[CH3:33])[CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 2829302-Chloro-4-iodoanilineHCID 2724682Lithium diisopropylamideHCID 22707302HCID 22707302, compound

Product 1

HCID 22707299HCID 22707299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring cold (−78° C.) solution comprised of 2-chloro-4-iodoaniline (1 molar equivalent) in anhydrous tetrahydrofuran under a nitrogen atmosphere is added a commercially available lithium diisopropylamide solution (Aldrich, 2.0 M in tetrahydrofuran/heptane/ethylbenzene, 1 molar equivalent). After stirring for 5 minutes, a solution comprised of 4-dimethylsulfamoyl-2-fluoro-benzoic acid (1 molar equivalent) in tetrahydrofuran is added. The cold bath is removed and the reaction mixture is stirred for 2 hours. The reaction mixture is then partitioned between diethyl ether and dilute aqueous hydrochloric acid. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford a product which may be purified by chromatography of recrystallization from an appropriate solvent like chloroform or heptane-ethanol.

Workup

  1. customTo a stirring cold (−78° C.) solution
  2. additionis added
  3. customThe cold bath is removed
  4. stirringthe reaction mixture is stirred for 2 hours
  5. customThe reaction mixture is then partitioned between diethyl ether and dilute aqueous hydrochloric acid
  6. washThe organic phase is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford a product which
  10. custommay be purified by chromatography of recrystallization from an appropriate solvent like chloroform or heptane-ethanol

Sources & evidence

ORD record
ord-b2230368f4104caa89e0b1556081ebae
Source dataset
uspto-grants-2002_08
Patent number
US06440966B1

Reaction notes

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