Triethylamine → N-Cyanoacetyl-2,4-dimethyl-5-nitroaniline

HRID 1074860Notes

Reaction equation

HRID 1074860 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[C:20]([CH2:22][C:23](Cl)=[O:24])#[N:21]>O1CCCC1>[C:20]([CH2:22][C:23]([NH:4][C:3]1[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]([CH3:9])=[CH:8][C:2]=1[CH3:1])=[O:24])#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2280072,4-Dimethyl-5-nitroanilineHCID 110515942-Cyanoacetyl chloride

Product 1

HCID 20494977N-Cyanoacetyl-2,4-dimethyl-5-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 76.6 g (0.455 mol) of 2,4-dimethyl-5-nitroaniline and 64 ml (0.46 mol) triethylamine in 500 ml abs. tetrahydrofurane is added dropwise within 1 h 47.2 g (0.455 mol) cyanoacetyl chloride in 100 ml tetrahydrofurane. After stirring for 2 h at 25° C. and 3 h at 80° C. and cooling to 25° C. the reaction mixture is filtered and poured into water. The precipitate is separated, washed with water and toluene/petrolether and dried. Yield: 84 g (78%) N-cyanoacetyl-2,4-dimethyl-5-nitroaniline, mp. 229°-230° C.

Workup

  1. temperaturecooling to 25° C. the reaction mixture
  2. filtrationis filtered
  3. additionpoured into water
  4. customThe precipitate is separated
  5. washwashed with water and toluene/petrolether
  6. customdried

Sources & evidence

ORD record
ord-c4cf14f6189c4074be60f2d30d9eb65f
Source dataset
uspto-grants-1983_07
Patent number
US04394156

Reaction notes

Loading…