Water → HCID 68692671, compound

HRID 2245000Notes

Reaction equation

HRID 2245000 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[OH2:11].[OH-:12].[Na+]>O1CCOCC1>[CH2:4]([CH:5]([NH:8][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10])[C:6]([OH:12])=[O:11])[C:3]#[C:2][CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium Hydroxide

Product 1

HCID 68692671HCID 68692671, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the solid (110 mg, 0.866 mmol) in 1N aq. NaOH (3 mL), a solution of 4-chlorophenyl isocyanate (200 mg, 1.30 mmol) in dioxane (3 mL) was added. The mixture was stirred at room temperature for 16 h. H2O (20 mL) was added. The aqueous layer was washed with Et2O, acidified with 4N HCl to pH 1-2. The product was extracted with EtOAc. The EtOAc solution was dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give the urea acid as a white powder (207 mg). MS 303.3 and 305.2 (M+Na, Cl pattern)

Workup

  1. washThe aqueous layer was washed with Et2O
  2. extractionThe product was extracted with EtOAc
  3. dry with materialThe EtOAc solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-51858845ab2840c19b9607b8600ce5a8
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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