Chloroacetyl isocyanate → HCID 66700265, compound

HRID 403672Notes

Reaction equation

HRID 403672 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([I:14])[C:11]=1[O:12][CH3:13])[NH2:8])([CH3:4])([CH3:3])[CH3:2].ClC[C:17]([N:19]=C=O)=[O:18].N12CCCN=C1CCCCC2>O1CCOCC1>[C:1]([C:5]1[CH:6]=[C:7]([NH:8][C:17]([NH2:19])=[O:18])[CH:9]=[C:10]([I:14])[C:11]=1[O:12][CH3:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 78209Chloroacetyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57419443HCID 57419443, compound

Product 1

HCID 66700265HCID 66700265, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-tert-butyl-5-iodo-4-methoxyaniline (915 mg, 3.0 mmol) in dioxane (20 mL) at 0° C. was added chloroacetyl isocyanate (0.256 mL, 3.00 mmol) dropwise to give a solution that was stirred at room temperature for 3 hours. 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.904 mL, 6.00 mmol) was added and the solution was stirred for 18 hours and partitioned between ethyl acetate and 1 M HCl. The ethyl acetate was washed with H2O, brine and dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified on an Isco 40 g silica cartridge eluting with methanol/dichloromethane (0% to 5%) to give the title compound.

Workup

  1. customto give a solution that
  2. stirringthe solution was stirred for 18 hours
  3. custompartitioned between ethyl acetate and 1 M HCl
  4. washThe ethyl acetate was washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on an Isco 40 g silica cartridge
  9. washeluting with methanol/dichloromethane (0% to 5%)

Sources & evidence

ORD record
ord-a44f64433eb245c3a7dec211d34bab0e
Source dataset
uspto-grants-2014_06
Patent number
US08748443B2

Reaction notes

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