2,6-Lutidine → Ethyl (o-chloro-alpha-ethoxybenzylidene)carbamate

HRID 2350937Notes

Reaction equation

HRID 2350937 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].N1C(C)=CC=CC=1C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[N:8][C:22](=[O:23])[O:24][CH2:25][CH3:26])[O:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 10928Ethyl chloroformateHCID 13092607Ethyl 2-chlorobenzimidate

Product 1

HCID 54317515Ethyl (o-chloro-alpha-ethoxybenzylidene)carbamate

Procedure

A mixture of 40 g (22 mmol) of ethyl o-chlorobenzimidate and 22.2 g (21 mmol) of 2,6-lutidine in 500 ml of petroleum ether (b.p. 100°-130° C.) is treated with 27.2 g (25 mmol) of ethyl chloroformate and the whole is then heated at reflux temperature for about 16 hours. The precipitated salt is subsequently filtered off, the filtrate is evaporated under reduced pressure and the residue is recrystallized from diethyl ether. In this manner there is obtained ethyl (o-chloro-α-ethoxybenzylidene)carbamate, m.p. 65°-66° C.; 1H--NMR (CDCl3, 60 MHz): 4.02 (q,OCH2CH3), 4.58 (q, OCH2CH3); mass spectrum: 220(100).

Workup

  1. temperaturethe whole is then heated
  2. temperatureat reflux temperature for about 16 hours
  3. filtrationThe precipitated salt is subsequently filtered off
  4. customthe filtrate is evaporated under reduced pressure
  5. customthe residue is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-06dc697a203f40638e4243d8da50899a
Source dataset
uspto-grants-1989_10
Patent number
US04871757

Reaction notes

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