3-(Trifluoromethyl)aniline → HCID 178509180, compound

HRID 2304438Notes

Reaction equation

HRID 2304438 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([NH:9][N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C1C=C(C=CC=1)N.C(#N)CC#N.O.[NH2:35][NH2:36]>>[NH2:15][C:14]1[C:11](=[N:10][NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=2)[C:12]([NH2:13])=[N:36][N:35]=1

Participants

5

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 911564HCID 911564, compound

Product 1

HCID 178509180HCID 178509180, compoundYield 31%

Procedure

This compound was prepared using 119 mg (0.5 mmol) of 2-[(3-trifluoromethylphenyl)-hydrazono]malononitrile, which was derived from 3-(trifluoromethyl)aniline (125 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 10 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 43 mg (31%) of the title compound as a yellow solid.

Workup

  1. customThis compound was prepared
  2. customPrecipitate formed in the reaction tube approximately 10 min
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-adff7387edf84b93a6f063a9a8f386df
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

Loading…