Triethylamine → 4-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

HRID 277186Notes

Reaction equation

HRID 277186 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1([CH3:21])[C:13]([N:18]=[C:19]=[O:20])=[CH:14][CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:20])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145334-Aminophenylacetic acidHCID 691942-Tolyl isocyanate

Product 1

HCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-aminophenylacetic acid (15.0 g) and o-tolylisocyanate (10.2 ml) in CH2Cl2 (200 ml) was added triethylamine (13.8 ml). After 1 h the resulting homogeneous solution was concentrated under reduced pressure, dissolved in water (100 ml) and acidified to pH 2 with 1N HCl. The off-white ppt was filtered, suspended in THF (200 ml) and 10 ml conc. HCl was added. The resulting homogeneous solution was concentrated under reduced pressure and recrystallized from EtOAc (800 ml) to give 22 g of the title compound as a white solid. MP 221-20° C.; MS [M+1]+285.2; Analysis calcd. for C16H16N203: C (67.59), H (5.67), N (9.85). Found: C (67.22), H (5.78), N (9.69).

Workup

  1. concentrationAfter 1 h the resulting homogeneous solution was concentrated under reduced pressure
  2. dissolutiondissolved in water (100 ml)
  3. filtrationThe off-white ppt was filtered
  4. addition10 ml conc. HCl was added
  5. concentrationThe resulting homogeneous solution was concentrated under reduced pressure
  6. customrecrystallized from EtOAc (800 ml)

Sources & evidence

ORD record
ord-d555c2bb91b94b018a94d8c79455fde1
Source dataset
uspto-grants-2002_03
Patent number
US06355662B1

Reaction notes

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