2-Chloro-5-nitrobenzotrifluoride → HCID 54090398, compound

HRID 1679537Notes

Reaction equation

HRID 1679537 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:12]([N+:30]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:33]([CH3:34])=[CH:32][CH:31]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].Cl[C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][C:43]=1[C:51]([F:54])([F:53])[F:52].C(N(C(C)C)CC)(C)C>C(#N)C>[N+:48]([C:45]1[CH:46]=[CH:47][C:42]([CH:34]=[C:33]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:30]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:31]=[CH:32]2)=[C:43]([C:51]([F:52])([F:53])[F:54])[CH:44]=1)([O-:50])=[O:49]

Participants

5

Reactant 3

HCID 612132-Chloro-5-nitrobenzotrifluorideHCID 81531DiisopropylethylamineHCID 20360937HCID 20360937, compound

Product 1

HCID 54090398HCID 54090398, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-octadecyllepidinium p-toluenesulfonate (24.6 g.), 2-chloro-5-nitrobenzotrifluoride (10 g.) and acetonitrile (700 ml.) was treated with diisopropylethylamine (20.7 g.) and refluxed for 6 hours with stirring. After filtering and evaporating, 1,4-dihydro-4-(4-nitro-2-trifluoromethylbenzylidene)-1-octadecylquinoline was formed. This colored dye was changed to the colorless compound having the formula: ##STR5## by reacting with a molar equivalent of p-toluenesulfonic acid in methanol.

Workup

  1. temperaturerefluxed for 6 hours
  2. filtrationAfter filtering
  3. customevaporating

Sources & evidence

ORD record
ord-68ef31cc4f6e4551af90e67a95b7a82b
Source dataset
uspto-grants-1978_03
Patent number
US04081275

Reaction notes

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