Hydrochloric Acid → 2-(2-Phenyldiazenyl)propanedinitrile

HRID 1747717Notes

Reaction equation

HRID 1747717 reaction equation
Cl.[N:2]([O-])=O.[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(=O)C.[Na+].[C:18](#[N:22])[CH2:19][C:20]#[N:21]>O.C(O)C>[C:7]1([N:6]=[N:2][CH:19]([C:18]#[N:22])[C:20]#[N:21])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8010MalononitrileHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 223472-(2-Phenyldiazenyl)propanedinitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Conc. hydrochloric acid (17.84 ml) and then a solution of 7.409 g (107.377 mmol) of sodium nitrite in water (18 ml) were added dropwise to 10.00 g (107.377 mmol) of aniline and ice (32 g) in an ice bath between 0° C. and 5° C., and the mixture was stirred at 0° C. for 30 min. At 0° C., a solution of 11.099 g (135.296 mmol) of sodium acetate in water (75 ml) was then added, and a solution of 7.049 g (107.377 mmol) of malononitrile in ethanol (6.5 ml) was subsequently added dropwise with stirring. After 2 h at 0° C., the resulting precipitate was filtered off with suction and washed with water (107 ml).

Workup

  1. stirringwith stirring
  2. waitAfter 2 h at 0° C.
  3. filtrationthe resulting precipitate was filtered off with suction
  4. washwashed with water (107 ml)

Sources & evidence

ORD record
ord-35d347b08df4458595158dc40d68326c
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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