Sodium Hydroxide → 4-[3-(1-Adamantyl)-4-methoxyphenylureido]benzoic acid

HRID 235312Notes

Reaction equation

HRID 235312 reaction equation
[OH-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([NH:21][C:22](=[O:34])[NH:23][C:24]4[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=4)[CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>CO>[C:3]12([C:13]3[CH:14]=[C:15]([NH:21][C:22](=[O:34])[NH:23][C:24]4[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=4)[CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH2:10][CH:9]3[CH2:11][CH:5]([CH2:6][CH:7]([CH2:8]3)[CH2:12]1)[CH2:4]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67714159Methyl 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoate

Product 1

HCID 677141384-[3-(1-Adamantyl)-4-methoxyphenylureido]benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6 g (0.15 mol) of sodium hydroxide are added to a solution of 6.08 g (14 mmol) of methyl 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoate in 75 ml of methanol and the mixture is stirred at room temperature for 3 hours and then heated to reflux for 3.5 hours. The reaction mixture is evaporated, the residue is then taken up with 100 ml of water and the mixture is acidified to pH 1. The solid is filtered off, rinsed with water, dried and recrystallized in a tetrahydrofuran/hexane mixture to yield 2.78 g (87%) of 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoic acid, melting point 279°-282° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3.5 hours
  3. customThe reaction mixture is evaporated
  4. filtrationThe solid is filtered off
  5. washrinsed with water
  6. customdried
  7. customrecrystallized in a tetrahydrofuran/hexane mixture

Sources & evidence

ORD record
ord-42fefcc204a84b329b19c50b141fe78c
Source dataset
uspto-grants-1997_01
Patent number
US05597839

Reaction notes

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