Triethylamine → 4-Chloro-2-[3-(2-fluoro-phenyl)-ureido]-benzoic acid

HRID 2262762Notes

Reaction equation

HRID 2262762 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][C:20]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[F:12])=[O:21])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666462-Amino-4-chlorobenzoic acidHCID 855882-Fluorophenyl isocyanate2×

Product 1

HCID 111626374-Chloro-2-[3-(2-fluoro-phenyl)-ureido]-benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Amino-4-chlorobenzoic acid (0.3 g), 2-fluorophenylisocyanate (0.2 ml) and triethylamine (0.24 ml) were stirred in toluene (20 ml) for a week. More 2-fluorophenylisocyanate (0.1 ml) was added and stirring continued for another week. The mixture was concentrated to almost dry, water was added and the pH was adjusted to 1 with diluted HCl. Water was decanted and the residue was dissolved in warm 96% EtOH. The pH was adjusted to 1 again with 4N HCl resulting in the precipitation of a solid, which was filtered and dried to give 4-chloro-2-[3-(2-fluoro-phenyl)-ureido]-benzoic acid (0.25 mg). Mp.=195-197° C. 4-Chloro-2-[3-(3-trifluromethyl-phenyl)-ureido]-benzenesulfonamide (Compound 10):

Workup

  1. waitcontinued for another week
  2. concentrationThe mixture was concentrated
  3. customto almost dry
  4. additionwater was added
  5. customWater was decanted
  6. dissolutionthe residue was dissolved in warm 96% EtOH
  7. customThe pH was adjusted to 1 again with 4N HCl resulting in the precipitation of a solid, which
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-9bf513c7b2164fb89463ccd036b29680
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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