Water → 3-[3-(4-Isopropyl-phenyl)-ureido]-benzoic acid

HRID 751002Notes

Reaction equation

HRID 751002 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1)([CH3:13])[CH3:12].O>CN(C)C=O>[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:22])[NH:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([OH:7])=[O:6])=[CH:16][CH:15]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 74193-Aminobenzoic AcidHCID 94416p-Isopropylphenyl isocyanate

Product 1

HCID 99262583-[3-(4-Isopropyl-phenyl)-ureido]-benzoic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-aminobenzoic acid (0.46 g, 3.4 mmol) in dimethylformamide (20 mL) at 0° C. was treated with 4-isopropylphenyl isocyanate (0.59 mL, 3.7 mmol). After stirring for 20 h, the solution was poured into 200 mL water, and the resulting precipitate was collected by filtration, washed with water and tetrahydrofuran, and dried under vacuum to afford the title product (0.85 g, 2.9 mmol, 85%) as a powder (m.p. 295-300° C.). TLC Rf 0.20 (ethyl acetate). 1H NMR (d6-DMSO, 300 MHz): δ 8.82 (1H, s), 8.57 (1H, s), 8.09 (1H, t, J=1.8 Hz), 7.58 (1H, dd, J=8.1, 1.1 Hz), 7.51 (1H, d, J=7.8 Hz), 7.36 (1H, t, J=8.0 Hz), 7.34 (2H, d, J=8.4 Hz), 7.12 (2H, d, J=8.4 Hz), 2.82 (1H, heptet, J=6.9 Hz), 1.17 (6H, d, J=6.9 Hz). MS (ES+): 299

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water and tetrahydrofuran
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f8bdde7f7cc741a3a65bd78ee20ef744
Source dataset
uspto-grants-2008_07
Patent number
US07405233B2

Reaction notes

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