N,N-dimethyl-3-(trifluoromethyl)aniline → HCID 86745106, compound

HRID 729052Notes

Reaction equation

HRID 729052 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[N:6]([CH3:8])[CH3:7].[CH3:14][C:15]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:16]=1[S:17]([OH:20])(=[O:19])=[O:18].C1(C)C=CC(S(OC)(=O)=O)=CC=1>CCOCC>[S:17]([C:16]1[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][CH:15]=1)([O-:20])(=[O:19])=[O:18].[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[N+:6]([CH3:14])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 5324699N,N-dimethyl-3-(trifluoromethyl)anilineHCID 86745107HCID 86745107, compound

Product 1

HCID 86745106HCID 86745106, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8.21 g (43.4 mmol) 3-(trifluoromethyl)-N,N-dimethylaniline and8.43 g (45.3 mmol) methyl p-toluenesulfonate (methyl tosylate) was mixed and heated to 80°±10° C. for 1.5 hr. The mixture was cooled and treated with ether, resulting in a suspension of fine powdery crystals. These were collected by filtration, washed with ether, and driedin a vacuum oven: 7.51 g (46.1%). The product was identified as 3-(trifluoromethyl)-N,N,N-trimethylanilinium tosylate by 1H NMR, IR,MS, and combustion analysis. Concentration of the filtrate yielded an additional 2.44 g (15.0%). The combined product was further purified by recrystallization from ethanol/toluene: mp 176.0°-178.2° C.; 1H NMR (CDCl3): δ 2.31 (s, 3H), 3.90 (s, 9H), 7.33 (aa`mm`, 4H), 7.59 (m 2H), 7.95 (m, 1H), and 8.40 ppm (m, 2H); IR (KBr): ν 1322, 1199, 1127, 812, and 689 cm-1 ; FDMS: m/e 204 amu (R4N+); anal. calcd. for C17H20F3NO3 (375.41): 3.7% N, 54.4% C, 5.4% H, and 15.2% F; found: 4.2, 4.6% N, 54.3, 54.4% C, 5.4, 5.7% H, and 15.3% F.

Workup

  1. temperatureheated to 80°±10° C. for 1.5 hr
  2. temperatureThe mixture was cooled
  3. customresulting in a suspension of fine powdery crystals
  4. filtrationThese were collected by filtration
  5. washwashed with ether
  6. customConcentration of the filtrate yielded an additional 2.44 g (15.0%)
  7. customThe combined product was further purified by recrystallization from ethanol/toluene

Sources & evidence

ORD record
ord-f71ddbafc921459893db102abc5f24ee
Source dataset
uspto-grants-1991_09
Patent number
US05051330

Reaction notes

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