Water → HCID 178441172, compound

HRID 1696501Notes

Reaction equation

HRID 1696501 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:15])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[Cl:14].[NH2:18][C:19]1[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[NH:21][N:20]=1.O>CN(C=O)C>[C:24]([C:22]1[CH:23]=[C:19]([NH:18][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=2[Cl:14])=[O:15])[NH:20][N:21]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 5227873-Amino-5-tert-butylpyrazoleHCID 67272012HCID 67272012, compound

Product 1

HCID 178441172HCID 178441172, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2,2-trichloroethyl-2,3-dichlorophenylcarbamate (0.400 g, 1.19 mmol) and 3-amino-5-t-butylpyrazole (0.165 g, 1.19 mmol) in DMF (1 mL) was stirred at 80° C. overnight. Water (50 mL) was added and the mixture was extracted with EtOAc (3×100 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 1-(3-t-butyl-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (230 mg, 59% yield) as a pink foam. 1H NMR (400 MHz, CDCl3): δ 8.26 (d, J=6.8 Hz, 1H), 7.20-7.14 (m, 2H), 5.85 (brs, 1H), 1.34 (s, 9H), amine and urea protons not visible; MS (EI) m/z: 327.0 (M+H+).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-5d5092043f9548b3b49cb1f0e15252bb
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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