3,5-Dichloro-4-(3,4-dichloro-alpha-cyanobenzyl)aniline → 3,5-Dichloro-4-(3,4-dichloro-alpha-cyanobenzyl)phenylhydrazine

HRID 321985Notes

Reaction equation

HRID 321985 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:20])[C:8]=1[CH:9]([C:18]#[N:19])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[NH2:5].[N:21]([O-])=O.[Na+]>C(O)(=O)C.O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:21])[CH:6]=[C:7]([Cl:20])[C:8]=1[CH:9]([C:18]#[N:19])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1

Participants

6

Reactant 2

HCID 220085763,5-Dichloro-4-(3,4-dichloro-alpha-cyanobenzyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 220085563,5-Dichloro-4-(3,4-dichloro-alpha-cyanobenzyl)phenylhydrazineYield 96%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

In 40 ml of acetic acid was dissolved 3.0 g of 3,5-dichloro-4-(3,4-dichloro-α-cyanobenzyl)aniline. To the solution was then added 3 ml of 35% hydrochloric acid. To the mixture was added dropwise, while cooling at temperatures ranging from 10 to 12° C., a solution of 0.8 g of 98.5% sodium nitrite in 3 ml of water. The reaction mixture was stirred for 40 minutes under the same conditions, to which was then added 7.0 g of stannous chloride dissolved in 10 ml of 35% hydrochloric acid. The reaction mixture was poured into ice-water, which was then made into alkaline, followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated to afford the titled compound in a yield of 96%, m.p.183-185° C.

Workup

  1. additionTo the mixture was added dropwise
  2. temperaturewhile cooling at temperatures
  3. customranging from 10 to 12° C.
  4. extractionfollowed by extraction with 200 ml of ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5f0c83252aa4451a9630f131a5f1d200
Source dataset
uspto-grants-2001_04
Patent number
US06211178B1

Reaction notes

Loading…