1-Tert-butyl-4-isocyanatobenzene → N-{4-[3-(4-tert-Butylphenyl)ureidomethyl]-2-fluoro-6-vinylphenyl}methanesulfonamide

HRID 2358431Notes

Reaction equation

HRID 2358431 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]([F:16])[CH:4]=1.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:29])[NH:1][CH2:2][C:3]2[CH:8]=[C:7]([CH:9]=[CH2:10])[C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]([F:16])[CH:4]=2)=[CH:23][CH:22]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 57665528HCID 57665528, compound

Product 1

HCID 11853001N-{4-[3-(4-tert-Butylphenyl)ureidomethyl]-2-fluoro-6-vinylphenyl}methanesulfonamideYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Aminomethyl-2-fluoro-6-vinylphenyl)methanesulfonamide (37.8 mg, 0.11 mmol), 1-tert-butyl-4-isocyanatobenzene (1.2 eq, 0.13 mmol, 22.49 μl), and TEA (3 eq, 0.33 mmol, 45.99 μl) were added in methylene chloride. The reaction mixture was stirred for 12 hrs. The reaction mixture was extracted with methylene chloride. A combined organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified with column chromatography (n-Hx:EA=1:1) to yield title compound (26.1 mg, 55%) as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride
  2. washA combined organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with column chromatography (n-Hx:EA=1:1)

Sources & evidence

ORD record
ord-508ca1d30fe643ab963c69de6623e90a
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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