tert-Butanol → N-(tert-Butoxycarbonyl)-[1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]amine

HRID 55359Notes

Reaction equation

HRID 55359 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:12][C:11](C(O)=O)=[N:10]1.C([N:26](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:48]([O-:51])(O)=[O:49].[Na+].[C:53](O)([CH3:56])([CH3:55])[CH3:54]>>[C:53]([O:51][C:48]([NH:26][C:11]1[CH:12]=[C:13]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:10]=1)=[O:49])([CH3:56])([CH3:55])[CH3:54]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 14772405-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 19957370N-(tert-Butoxycarbonyl)-[1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]amine

Procedure

3.25 g of the 1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrazole-3-carboxylic acid obtained according to Example 1C) and then 1.32 ml of triethylamine are added to a solution of 2.05 ml of diphenylphosphoryl azide in 40 ml of anhydrous t-butanol and the reaction mixture is refluxed under nitrogen for 12 hours. After cooling, it is treated with a saturated solution of NaHCO3 and extracted with ethyl acetate. After washing with water and then with a saturated solution of NaCl, drying over MgSO4 and evaporation of the solvents, the crude product is purified by chromatography on 70-230 mesh silica gel using CH3OH/CH2Cl2 1/99 (v/v) as the eluent to give 1.09 g of the expected product.

Workup

  1. temperaturethe reaction mixture is refluxed under nitrogen for 12 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialwith a saturated solution of NaCl, drying over MgSO4 and evaporation of the solvents
  6. customthe crude product is purified by chromatography on 70-230 mesh silica gel

Sources & evidence

ORD record
ord-04468ee7ec334cba8d7a8a0d96adecf8
Source dataset
uspto-grants-1997_04
Patent number
US05624941

Reaction notes

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