Urea → HCID 12023321, compound

HRID 2236567Notes

Reaction equation

HRID 2236567 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2].[NH2:15]C(N)=O>>[Cl:14][C:12]1[CH:13]=[C:5]2[C:6](=[CH:10][CH:11]=1)[C:7](=[O:8])[NH:15][C:1](=[O:2])[CH2:4]2

Participants

3

Reactant 2

HCID 1176UreaHCID 3340352-(Carboxymethyl)-4-chlorobenzoic acid

Product 1

HCID 12023321HCID 12023321, compoundYield 34%

Procedure

An amount of 2-(carboxymethyl)-4-chlorobenzoic acid (8.4 g, 39.14 mmol) and 2.82 g (47 mmol) of urea is vigorously stirred at 160° C. Solids were melted, boiled and hardened after 15 min. Continue to heat and blow nitrogen through to remove water generated from reaction until total dryness. After cooling, the solid is ground to fine powder. After successively washing with saturated NaHCO3 solution, water, methanol, ether and hexane, the powder is dried in oven (60° C.) overnight to give 2.6 g (34.0% yield) of light yellow solid: MS (ESI) m/z 194.0 (M−H)−1 Analysis for C9H6ClNO2, Calcd: C, 55.26; H, 3.09; N, 7.16. Found: C, 54.86; H, 2.96; N, 7.12

Workup

  1. temperatureto heat
  2. customto remove water
  3. customgenerated from reaction until total dryness
  4. temperatureAfter cooling
  5. washAfter successively washing with saturated NaHCO3 solution, water, methanol, ether and hexane
  6. customthe powder is dried in oven (60° C.) overnight
  7. customto give 2.6 g (34.0% yield) of light yellow solid

Sources & evidence

ORD record
ord-4a9437c76226460d995d0aaa045cb8c5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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