4-Aminobenzoic Acid → 4-(methylcarbamoylamino)benzoic acid

HRID 1451059Notes

Reaction equation

HRID 1451059 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12]=[C:13]=[O:14]>C(Cl)(Cl)Cl>[CH3:11][NH:12][C:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:14]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 12228Methyl Isocyanate

Product 1

HCID 3062384-(methylcarbamoylamino)benzoic acidYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3.0 g (0.22 mol) of 4-aminobenzoic acid (Aldrich) in 100 mL of chloroform was treated with 10 g (0.175 mol) of methylisocyanate (Aldrich), and the mixture was stirred at ambient temperatures for three days. The mixture was concentrated and the residue was triturated with diethyl ether/petroleum ether. The solid was collected by filtration, air-dried, and then slurried with 100 mL of water. The solid was collected by vacuum filtration and the cake was sucked dry. The cake was then recrystallized from acetonitrile/water to yield 1.8 g (43%) of the title compound as a fluffy white solid, mp>400° C. (lit1 mp>300° C.).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with diethyl ether/petroleum ether
  3. filtrationThe solid was collected by filtration
  4. customair-dried
  5. filtrationThe solid was collected by vacuum filtration
  6. customthe cake was sucked dry
  7. customThe cake was then recrystallized from acetonitrile/water

Sources & evidence

ORD record
ord-2025850caf0d414d8939b4724f75664d
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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