1-Tert-butyl-4-isocyanatobenzene → HCID 11853002, compound

HRID 2358434Notes

Reaction equation

HRID 2358434 reaction equation
[NH2:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH:14]=[CH2:15])(=[O:13])=[O:12])=[C:6]([CH:16]=[CH2:17])[CH:5]=1)[CH3:3].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>>[C:18]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:30])[NH:1][CH:2]([C:4]2[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH:14]=[CH2:15])(=[O:13])=[O:12])=[C:6]([CH:16]=[CH2:17])[CH:5]=2)[CH3:3])=[CH:24][CH:23]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 68457029HCID 68457029, compound

Product 1

HCID 11853002HCID 11853002, compoundYield 200%

Procedure

Ethenesulfonic acid [4-(1-amino-ethyl)-2-vinyl-phenyl]-amide (15.6 mg, 0.04 mmol), 4-tert-butyl phenylisocyanate (1.2 eq, 0.053 mmol, 9.45 μl), and TEA (1.2 eq, 0.12 mmol, 16.73 μl) were added in MC. The reaction mixture was stirred for 5 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=3:1->2:1) to yield title compound (34.2 mg, 40%).

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=3:1->2:1)

Sources & evidence

ORD record
ord-1986bfc79fcc4f6fa04b20c376e33ce5
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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