3-Nitroaniline → HCID 14880506, compound

HRID 1588843Notes

Reaction equation

HRID 1588843 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[C:11]1([N:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:18]([CH2:20][NH:21][C:22](N2C=CN=C2)=[O:23])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:22](=[O:23])[NH:21][CH2:20][C:18]([N:17]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:19])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74233-NitroanilineHCID 19754769HCID 19754769, compound

Product 1

HCID 14880506HCID 14880506, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Nitroaniline (2.8 g) is added to a solution of N-(diphenylcarbamoylmethyl)-1-imidazolecarboxamide (3.2 g) in anhydrous toluene (35 cc). The solution obtained is stirred under reflux for 4 hours. After cooling, the reaction mixture is washed with an N aqueous solution (40 cc) of methanesulphonic acid and distilled water (2×30 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue is stirred for 20 minutes in dichloromethane (25 cc). The insoluble product is separated by filtration, washed with dichloromethane (5 cc) and dried in the air. After recrystallization in ethyl acetate, 2-[3-(3-nitrophenyl)ureido]-N,N-diphenylacetamide (0.7 g), m.p. 180° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with an N aqueous solution (40 cc) of methanesulphonic acid
  5. distillationdistilled water (2×30 cc)
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. stirringThe residue is stirred for 20 minutes in dichloromethane (25 cc)
  10. customThe insoluble product is separated by filtration
  11. washwashed with dichloromethane (5 cc)
  12. customdried in the air
  13. customAfter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-5e249435acca4cf0b37a8205d9b83bc3
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

Loading…