Triethylamine → HCID 20096579, compound

HRID 1769974Notes

Reaction equation

HRID 1769974 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[CH:7]=[C:6]([N:18]=[CH:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 753995-Fluoro-2-nitroaniline

Product 1

HCID 20096579HCID 20096579, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 15.6 g (100 mmol) 2-amino-4-fluoronitrobenzene, 22.5 g (180 mmol) 4-fluorobenzylamine and 20.2 g (220 mmol) triethylamine in 150 ml dimethylsulfoxide is heated with stirring and under an inert gas atmosphere for 30 hours to 60°-70° C. When the reaction time is completed, the solvent is distilled off in a vacuum, the residue is taken up in 500 ml 0.5N hydrochloric acid and the mixture is stirred intensively at room temperature for 30 minutes. The precipitated solid is suction filtered and subjected to hot steam extraction with toluene. The product crystallizing out of the toluene after the mixture has been allowed to stand for twelve hours at 0°-4° C. is suction filtered and dried in a vacuum. 22.2 g (85 % of theory) are obtained. After being left to stand for 12 hours at 0°-4° C., 2-amino-4-(4-fluorobenzylamino)-nitrobenzene crystallizes out of the toluene phase as orange-yellow crystals.

Workup

  1. distillationthe solvent is distilled off in a vacuum
  2. stirringthe mixture is stirred intensively at room temperature for 30 minutes
  3. filtrationfiltered
  4. extractionsubjected to hot steam extraction with toluene
  5. customThe product crystallizing out of the toluene after the mixture
  6. waitto stand for twelve hours at 0°-4° C.
  7. filtrationfiltered
  8. customdried in a vacuum
  9. custom22.2 g (85 % of theory) are obtained
  10. waitAfter being left
  11. waitto stand for 12 hours at 0°-4° C.
  12. custom2-amino-4-(4-fluorobenzylamino)-nitrobenzene crystallizes out of the toluene phase as orange-yellow crystals

Sources & evidence

ORD record
ord-adb74b9b81ca4fffb915b0d02280996b
Source dataset
uspto-grants-1995_01
Patent number
US05384330

Reaction notes

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