Sodium Hydroxide → 3-Ureidomethyl-phthalic acid

HRID 448433Notes

Reaction equation

HRID 448433 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:21])[C:6]1[C:7](=[C:12]([CH2:16][NH:17][C:18]([NH2:20])=[O:19])[CH:13]=[CH:14][CH:15]=1)[C:8]([O:10]C)=[O:9]>O.C(O)C>[NH:17]([CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:6]([C:5]([OH:21])=[O:4])[C:7]=1[C:8]([OH:10])=[O:9])[C:18]([NH2:20])=[O:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 672293263-Ureidomethyl-phthalic acid dimethyl ester

Product 1

HCID 672298293-Ureidomethyl-phthalic acidYield 79.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.4 g, 10.5 mmol) in water (10 mL) was added to a stirred suspension of 3-ureidomethyl-phthalic acid dimethyl ester (1.4 g, 5.3 mmol) in ethanol (30 mL). The mixture was refluxed for one hour and then cooled to room temperature. The mixture was concentrated, and the residue was dissolved in water (30 mL). The mixture was acidified with 4N HCl to pH 1. The mixture was filtered to give 3-ureidomethyl-phthalic acid (1.0 g, 76%): 1H NMR (DMSO-d6) δ 4.22 (d, J=5.9 Hz, 2H, CH2), 5.68 (s, 2H, NH2), 6.40 (t, J=6.0 Hz, 1H, NH), 7.46-7.56 (m, 2H, Ar), 7.73 (d, J=6.9 Hz, 1H, Ar), 13.23 (b, 2H).

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in water (30 mL)
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-9393a3bc94ee44bfb39e9699d66ec78e
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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