Aniline → HCID 840542, compound

HRID 1921290Notes

Reaction equation

HRID 1921290 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(C(C)C)C(C)C.ClC(Cl)(Cl)C(O[C:26](=[O:31])C(Cl)(Cl)Cl)=O.[C:34]1([NH2:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:26]([NH:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6115AnilineHCID 83904-Methyl-3-nitroanilineHCID 20079Trichloroacetic anhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 840542HCID 840542, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution (4-methyl-3-nitrophenyl)amine (152 mg) in CH2Cl2 (15 mL) were added iPr2NEt (1.29 g) and trichloroacetic anhydride (370 mg) successively at 0° C. under a nitrogen atmosphere, and the mixture was stirred at 0° C. for 3 hr. To the solution was added phenylamine (930 mg), and the resulted mixture was stirred at room temperature for 16 h. The volatile materials were evaporated in vacuo. The residue was diluted with EtOAc (10 mL) and the resulted mixture was successively washed with 1M HCl (5 mL×2), saturated aqueous NaHCO3 (5 mL×2) and brine, dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was triturated with IPE. The precipitates produced were collected by filtration to give 1-(4-methyl-3-nitrophenyl)-3-phenylurea (270 mg).

Workup

  1. stirringthe resulted mixture was stirred at room temperature for 16 h
  2. customThe volatile materials were evaporated in vacuo
  3. additionThe residue was diluted with EtOAc (10 mL)
  4. washthe resulted mixture was successively washed with 1M HCl (5 mL×2), saturated aqueous NaHCO3 (5 mL×2) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was triturated with IPE
  9. customThe precipitates produced
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-9dc2bd7ad35242cf8f03a89302f0e234
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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