Chloroform → HCID 86234922, compound

HRID 2414116Notes

Reaction equation

HRID 2414116 reaction equation
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])#[N:12].[OH-].[Na+].C(Cl)(Cl)Cl>CC(C)=O>[C:11]([N:13]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])[C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([N:13]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])[C:11]#[N:12])=[O:7])#[N:12]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 61034Adipoyl chlorideHCID 20153942HCID 20153942, compound

Product 1

HCID 86234922HCID 86234922, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 10.07 g (0.055 mol) of adipyl chloride in 30 ml of acetone is added dropwise to 14.6 g (0.1 mol) of N-cyano-2,4-dimethylaniline in 60 ml of 2N NaOH (0.12 mol) at 10°-26° C. in the course of 40 minutes, while cooling and stirring rapidly, and the reaction mixture is then stirred for another 2 hours and 15 minutes at 15°-25° C. 50 ml of chloroform are then added, the mixture is stirred for 10 minutes, the two phases are separated, the organic phase is dried with anhydrous sodium sulfate, the suspension is filtered with suction and the filtrate is concentrated on a rotary evaporator at 40° C. in vacuo. The residue is recrystallised from 113 ml of ethyl acetate to give 18.7 g (93.0% of theory) of a colourless, crystalline compound with a melting point of 120°-122.2° C.

Workup

  1. temperaturewhile cooling
  2. stirringthe reaction mixture is then stirred for another 2 hours and 15 minutes at 15°-25° C
  3. stirringthe mixture is stirred for 10 minutes
  4. customthe two phases are separated
  5. dry with materialthe organic phase is dried with anhydrous sodium sulfate
  6. filtrationthe suspension is filtered with suction
  7. concentrationthe filtrate is concentrated on a rotary evaporator at 40° C. in vacuo
  8. customThe residue is recrystallised from 113 ml of ethyl acetate
  9. customto give 18.7 g (93.0% of theory) of a colourless, crystalline compound with a melting point of 120°-122.2° C.

Sources & evidence

ORD record
ord-3b6dee333c484261aed298b0285cc4db
Source dataset
uspto-grants-1988_01
Patent number
US04721770

Reaction notes

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