Methyl 4-aminobenzoate → Methyl 4-[[(methylamino)carbonyl]amino]benzoate

HRID 439823Notes

Reaction equation

HRID 439823 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]=[C:14]=[O:15]>C1(C)C=CC=CC=1>[CH3:12][NH:13][C:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)=[O:15]

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 12228Methyl Isocyanate2×

Product 1

HCID 726385Methyl 4-[[(methylamino)carbonyl]amino]benzoateYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-aminobenzoate (15 g, 99 mmol), and methyl isocyanate (11.8 mL, 200 mmol) in toluene (400 mL) was heated at 100° C. under N2 for 3 hours during which time a precipitate formed slowly. Additional methyl isocyanate (11.8 mL, 200 mmol) was added and heating was continued for 2 hours. The reaction mixture was cooled to 0° C. and filtered. The precipitate was washed with ether and vacuum-dried to give methyl 4-(N-methylaminocarbonyl)aminobenzoate as a colorless solid (17.5 g, 85%).

Workup

  1. customformed slowly
  2. temperatureheating
  3. filtrationfiltered
  4. washThe precipitate was washed with ether
  5. customvacuum-dried

Sources & evidence

ORD record
ord-e228e0b3c62443c79407176e248b6281
Source dataset
uspto-grants-1996_05
Patent number
US05516795

Reaction notes

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