Ethanesulfonyl chloride → HCID 67073865, compound

HRID 1852391Notes

Reaction equation

HRID 1852391 reaction equation
[NH2:1][C:2]1[C:3]([CH3:28])=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][C:6]1[C:7]([N+:22]([O-:24])=[O:23])=[C:8]([CH:18]=[C:19]([F:21])[CH:20]=1)[NH:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[F:17].[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[F:21][C:19]1[CH:18]=[C:8]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:7]([N+:22]([O-:24])=[O:23])=[C:6]([CH:20]=1)[O:5][C:4]1[C:3]([CH3:28])=[C:2]([NH:1][S:31]([CH2:29][CH3:30])(=[O:33])=[O:32])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 67074413HCID 67074413, compound

Product 1

HCID 67073865HCID 67073865, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

1.18 g 3-(3-amino-2-methylphenoxy)-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (2.3 mmol, 1 eq.) were dissolved in 9.6 mL pyridine, cooled to 0° C., treated with 292 μL ethyl sulfonyl chloride (3.1 mmol, 1.2 eq.) and stirred at 0° C. for 3 hours. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The aqueous layer was reextracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated in vacuo to yield 1.6 g of the crude product, which was taken up in toluene and again concentrated in vacuo. The crude product was used in the subsequent transformations without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and ethyl acetate
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c368f4071e464d6098f69d58be5101cc
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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