Phenyl isocyanate → 4-Chloro-2-[[(phenylamino)carbonyl]amino]benzoic acid

HRID 2111964Notes

Reaction equation

HRID 2111964 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].[C:12]1([N:18]=[C:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][C:19]([NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:20])[CH:10]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 103344344-Chloro-2-[[(phenylamino)carbonyl]amino]benzoic acidYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-chloro-benzoic acid (515 mg, 3.0 mmol) was suspended in dry THF (5 ml) and phenylisocyanate (429 mg, 3.6 mmol) was added. Triethylamine (303 mg, 3.0 mmol) was added and the mixture was stirred for 2 hours. The mixture was diluted with 75 ml ethyl acetate and extracted into 150 ml 1 M aqueous NaOH, and washed once with 50 ml ethyl acetate. The aqueous phase was then acidified with 4 M aqueous HCl and the product extracted with 2×100 ml ethyl acetate. The organic solvent was dried (Na2SO4) and reduced under vacuum, and the product recrystallised from acetone/water to yield 680 mg (78%) of off-white crystals (m.p. 186-188° C.).

Workup

  1. extractionextracted into 150 ml 1 M aqueous NaOH
  2. washwashed once with 50 ml ethyl acetate
  3. extractionthe product extracted with 2×100 ml ethyl acetate
  4. dry with materialThe organic solvent was dried (Na2SO4)
  5. customthe product recrystallised from acetone/water

Sources & evidence

ORD record
ord-0eabe208bb3d4d5db2116b0468dbf78d
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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