2,2,2-Trichloroethyl chloroformate → HCID 54204825, compound

HRID 67711Notes

Reaction equation

HRID 67711 reaction equation
[S-:1][C:2]#[N:3].[K+].Cl[C:6]([O:8][CH2:9][C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7].[CH2:14]([N:16]([CH2:26][CH3:27])/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH3:15]>C1OCCOCCOCCOCCOCCOC1.C1(C)C=CC=CC=1>[CH2:26]([N:16]([CH2:14][CH3:15])[CH:17]=[C:18]([C:2](=[S:1])[NH:3][C:6]([O:8][CH2:9][C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH3:27]

Participants

6

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 516872Potassium thiocyanateHCID 204932262-Cyanoethyl trans-3-diethylaminoacrylate

Product 1

HCID 54204825HCID 54204825, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 55.4 g (0.57 moles) of potassium thiocyanate, 1 g of 18-crown-6 cyclic ether, 80.5 g (0.38 moles) of 2,2,2-trichloroethyl chloroformate and 300 ml of toluene was heated for 3 hours at 50° C. to prepare the acyl isothiocyanate. The mixture was filtered and 74 g (0.38 moles) of 2-cyanoethyl trans-3-diethylaminoacrylate were added dropwise over one hour. After 24 hours at room temperature, the mixture was filtered to give 108 g of crude material which was recrystallized from toluene to give 63 g of pure adduct, melting point 116° to 118° C.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe mixture was filtered
  3. customto give 108 g of crude material which
  4. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-1f2a129973b0467491faa4c6c9fcf5e1
Source dataset
uspto-grants-1982_08
Patent number
US04346161

Reaction notes

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