2,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone → N-[2,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethylidene]-N'-(2,4,6-triisopropylbenzenesulfonyl)hydrazine

HRID 1377943Notes

Reaction equation

HRID 1377943 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=O.[CH:17]([C:20]1[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[C:22]([CH:29]([CH3:31])[CH3:30])[C:21]=1[S:32]([NH:35][NH2:36])(=[O:34])=[O:33])([CH3:19])[CH3:18]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:16])([F:15])[C:3](=[N:36][NH:35][S:32]([C:21]1[C:22]([CH:29]([CH3:30])[CH3:31])=[CH:23][C:24]([CH:26]([CH3:28])[CH3:27])=[CH:25][C:20]=1[CH:17]([CH3:19])[CH3:18])(=[O:33])=[O:34])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1

Participants

5

Reactant 2

HCID 1365592,2,2-Trifluoro-3'-(trifluoromethyl)acetophenoneHCID 3593332,4,6-Triisopropylbenzenesulphonohydrazide

Product 1

HCID 57173824N-[2,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethylidene]-N'-(2,4,6-triisopropylbenzenesulfonyl)hydrazineYield 49.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone (3.7 g, 0.15 mol) was dissolved in dichloromethane (15 ml, anhydrous) and the solution was cooled to 0° C. Titanium tetrachloride (15 ml, 1.0M in dichloromethane) was added to the solution dropwise and the resulting ochre suspension was stirred at room temperature for 12 h. 2,4,6-Triisopropylbenzenesulfonyl hydrazine (3.8 g, 0.015 mol) was added to the suspension and the reaction mixture was stirred for 2 h. The mixture was quenched with water and the organic phase was separated, washed with brine, dried and the solvent was removed in vacuo. The resulting solid was purified by column chromatography using 10-25% ethyl acetate in hexane as eluant. This afforded the product as a white crystalline solid (3.9 g). 1HNMR (250 MHz, CDCl3) δ 1.10-1.22 (m, 18H, (CH3)2), 2.86 (septet, 1H, C H(CH3)2), 4.02 (septet, 2H, C H(CH3)2), 7.14 (S, 2H, ArH), 7.40-7.48 (m, 2H, ArH), 7.64 (t, 1H, ArH), 7.72-7.80 (m, 1H, ArH), 8.72 (s, 1H, NH).

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. customThe mixture was quenched with water
  3. customthe organic phase was separated
  4. washwashed with brine
  5. customdried
  6. customthe solvent was removed in vacuo
  7. customThe resulting solid was purified by column chromatography

Sources & evidence

ORD record
ord-47084093767747a28210698085276609
Source dataset
uspto-grants-1997_09
Patent number
US05665883

Reaction notes

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