2-(Ethoxymethylene)propanedinitrile → HCID 57504742, compound

HRID 1098280Notes

Reaction equation

HRID 1098280 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:4]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C>>[NH2:20][C:19]1[N:10]([C:4]2[C:5]([F:9])=[CH:6][CH:7]=[CH:8][C:3]=2[Cl:2])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Participants

3

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 27737302-Chloro-6-fluorophenylhydrazine hydrochloride

Product 1

HCID 57504742HCID 57504742, compound

Conditions

Temperature
0 °C

Procedure

(2-Chloro-6-fluorophenyl)hydrazine hydrochloride (CAS no. 529512-79-6) (5 g, 25.38 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL). The organic layer separated and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated. The resultant oil was suspended in MeOH (50 mL) under nitrogen at -5° C. 2-(Ethoxymethylene)malononitrile (3.10 g, 25.38 mmol) added portionwise over 5 mins and the mixture stirred at ˜0° C. for 30 mins. The reaction mixture was allowed to warm to room temperature and then heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (3.52 g) which was used without further purification.

Workup

  1. custom529512-79-6) (5 g, 25.38 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL)
  2. customThe organic layer separated
  3. washwashed with water (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwas suspended in MeOH (50 mL) under nitrogen at -5° C
  8. temperatureto warm to room temperature
  9. temperatureheated
  10. temperatureat reflux under nitrogen for 2 hours
  11. temperatureto cool
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-724821fbb4ee4b518875c302d519b372
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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