Toluene → HCID 12674641, compound

HRID 866643Notes

Reaction equation

HRID 866643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[N:12]=[C:13]1[NH:17][CH2:16][CH2:15][NH:14]1.CN(C)C.[C:22]1([CH3:28])[CH:27]=[CH:26]C=CC=1>>[CH:27]1([CH2:26][N:12]([C:13]2[NH:17][CH2:16][CH2:15][N:14]=2)[C:3]2[C:4]([C:8]([F:11])([F:10])[F:9])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:22][CH2:28]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 1146TrimethylamineHCID 178505687HCID 178505687, compound

Product 1

HCID 12674641HCID 12674641, compoundYield 58.4%

Conditions

Temperature
120 °C

Procedure

A mixture consisting of 8 gm (0.032 mol) of 2-[(2-fluoro-6-trifluoromethyl-phenyl)-imino]-imidazolidine, 4.6 gm (105% of the stoichiometrically required amount), 5 cc of trimethylamine acid 25 ml of absolute toluene was heated at 120° C for 18 hours in a closed tube. After cooling, the liquid phase was decanted, the solid residue was dissolved in about 150 cc of 1N hydrochloric acid, the solution was extracted several times with ether, and the ethereal extracts were discarded. The acidic aqueous phase and fractionally extracted with ether at stepwisely increasing pH-values (alkalization with dilute sodium hydroxide). The thin-layer chromatographically uniform fractions were combined, dried over Drierite (calcium sulfate) and evaporated to dryness in vacuo. The residue was caused to crystallize by stirring it with petroleum ether, the mixture was suction-filtered, and the filter cake was dried, yielding 5.7 gm (58.4% of theory) of 2-[N-(cyclopropyl-methyl)-N-(2-fluoro-6-trifluoromethyl-phenyl)-amino]-2-imidazoline, m.p. 126°-127° C.

Workup

  1. temperatureAfter cooling
  2. customthe liquid phase was decanted
  3. dissolutionthe solid residue was dissolved in about 150 cc of 1N hydrochloric acid
  4. extractionthe solution was extracted several times with ether
  5. extractionThe acidic aqueous phase and fractionally extracted with ether at stepwisely increasing pH-values (alkalization with dilute sodium hydroxide)
  6. dry with materialdried over Drierite (calcium sulfate)
  7. customevaporated to dryness in vacuo
  8. customto crystallize
  9. filtrationthe mixture was suction-filtered
  10. customthe filter cake was dried

Sources & evidence

ORD record
ord-f1bacfec44ad43329cccaca048e16b5d
Source dataset
uspto-grants-1978_07
Patent number
US04100292

Reaction notes

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