Urea → 4-Chloro-3-ureido-benzoic acid

HRID 1485980Notes

Reaction equation

HRID 1485980 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].[NH2:12][C:13](N)=[O:14]>C(O)(=O)C>[Cl:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:13]([NH2:12])=[O:14]

Participants

4

Reactant 2

HCID 1176UreaHCID 760923-Amino-4-chlorobenzoic acid

Product 1

HCID 246890454-Chloro-3-ureido-benzoic acidYield 81.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 3-amino-4-chlorobenzoic acid (34.2 g, 200 mmol) and urea (24 g, 400 mmol) in glacial acetic acid (200 mL) was heated at 100° C. for 24 h. The mixture was allowed to cool to room temperature and the resulting precipitate was separated by filtration, washed with water (2×100 mL) and diethyl ether (2×100 mL), then air dried to give 35 g of 4-chloro-3-ureido-benzoic acid as a grey solid that was carried on without further purification.

Workup

  1. customthe resulting precipitate was separated by filtration
  2. washwashed with water (2×100 mL) and diethyl ether (2×100 mL)
  3. customair dried

Sources & evidence

ORD record
ord-b2b99b28d5844b08a414649de01aa0c5
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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