Trichloroacetonitrile → (1Z)-Trichloro-N'-(2-ethoxyethyl)ethanimidamide

HRID 905357Notes

Reaction equation

HRID 905357 reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].[CH2:7]([O:9][CH2:10][CH2:11][NH2:12])[CH3:8]>>[CH2:7]([O:9][CH2:10][CH2:11][NH:12][C:3](=[NH:4])[C:2]([Cl:6])([Cl:5])[Cl:1])[CH3:8]

Participants

3

Reactant 2

HCID 11011TrichloroacetonitrileHCID 66970Ethoxyethylamine

Product 1

HCID 178467948(1Z)-Trichloro-N'-(2-ethoxyethyl)ethanimidamide

Conditions

Temperature
0 °C

Procedure

To 15 ml (0.5 mole) trichloroacetonitrile in an ice bath, was added 8.9 g (0.10 mole) 2-ethoxyethylamine. The addition was carried out over 20 minutes and the reaction temperature rose to 35° C. After 20 minutes additional stirring at 0° C., it was stirred at room temperature overnight. The mixture was washed to give 12.0 g. Distillation yielded: (1) 9.1 g (B.P. 0.41 mm, 92°-97° C.); (2) 1.9 g (B.P. 0.41 mm, 96° C.). Total yield: 10.9 g (47%). The structure was confirmed via IR, VPC, and elemental analysis.

Workup

  1. additionThe addition
  2. customrose to 35° C
  3. stirringit was stirred at room temperature overnight
  4. washThe mixture was washed
  5. customto give 12.0 g
  6. distillationDistillation
  7. customyielded

Sources & evidence

ORD record
ord-2798194667c14e8a985bda433be5ff65
Source dataset
uspto-grants-1983_12
Patent number
US04423246

Reaction notes

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