4-Methyl-3-nitroaniline → 1-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-3-(4-methyl-3-nitrophenyl)urea

HRID 1921288Notes

Reaction equation

ClC(Cl)(Cl)C[O:4][C:5](=O)[NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:10]=[C:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:8]=1.[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][C:28]=1[N+:34]([O-:36])=[O:35].CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[C:19]([C:9]1[CH:8]=[C:7]([NH:6][C:5]([NH:33][C:30]2[CH:31]=[CH:32][C:27]([CH3:26])=[C:28]([N+:34]([O-:36])=[O:35])[CH:29]=2)=[O:4])[N:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:10]=1)([CH3:21])([CH3:20])[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2,2,2-trichloroethyl[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]carbamate (101 mg) and (4-methyl-3-nitrophenyl)amine (38 mg) in DMSO (1 mL) was added iPr2NEt (44 under a nitrogen atmosphere and the mixture was stirred at 60° C. for 4 hr. The reaction mixture was diluted with EtOAc (2 mL) and successively washed with 1M HCl (2 mL×2), saturated aqueous NaHCO3 (2 mL) and brine (2 mL), dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was purified by silica gel column chromatography eluting with 2% MeOH in CH2Cl2 to give 1-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-3-(4-methyl-3-nitrophenyl)urea (96 mg).

Workup

washsuccessively washed with 1M HCl (2 mL×2), saturated aqueous NaHCO3 (2 mL) and brine (2 mL)
dry with materialdried over MgSO4
filtrationfiltered
customThe filtrate was evaporated in vacuo
customthe residue was purified by silica gel column chromatography
washeluting with 2% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-dc4ca955ec2d495fac760c111f0b8eac
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173684B2

Reaction notes

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