Ammonium Hydroxide → HCID 69659402, compound

HRID 1829060Notes

Reaction equation

HRID 1829060 reaction equation
[N:1]([CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[O:6]1)=[C:2]=[O:3].[NH4+:24].[OH-]>C1COCC1>[O:23]=[C:15]1[C:14](=[C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]([CH2:4][NH:1][C:2]([NH2:24])=[O:3])[O:6]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86590934HCID 86590934, compound

Product 1

HCID 69659402HCID 69659402, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-Isocyanatomethyl-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (65 mg, 0.21 mmol) in THF (4 ml) at room temperature was added concentrated NH4OH (2 ml). The reaction was stirred 5 minutes and then partitioned between EtOAc and water. The organic layer was washed with very dilute HCl, brine, dried with anhydrous Na2SO4 and rotary evaporated to obtain a solid. The solid was recrystallized from EtOAc/MeOH to give [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-ylmethyl]-urea as a yellow solid (46 mg, 68%).

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with very dilute HCl, brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customrotary evaporated
  5. customto obtain a solid
  6. customThe solid was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-9c77f8f6aa824a56944a47156a18747f
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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