Methyl chloroglyoxylate → HCID 19899222, compound

HRID 1196640Notes

Reaction equation

HRID 1196640 reaction equation
[C:1](Cl)([C:3]([O:5][CH3:6])=[O:4])=[O:2].[F:8][C:9]1[CH:30]=[CH:29][C:12]([O:13][C:14]2[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1>ClCCCl.CN(C)C1C=CN=CC=1>[C:1]([N:21]([CH2:20][CH2:19][O:18][C:17]1[CH:27]=[CH:28][C:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([F:8])=[CH:30][CH:29]=2)=[CH:15][CH:16]=1)[C:22](=[O:26])[O:23][CH2:24][CH3:25])([C:3]([O:5][CH3:6])=[O:4])=[O:2]

Participants

5

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 19899217HCID 19899217, compound

Product 1

HCID 19899222HCID 19899222, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

With stirring and under nitrogen, a solution of methoxalyl chloride in 10 ml of 1,2-dichloroethane is added dropwise at +80° C. over 20 minutes to a solution of 10.0 g of ethyl 2-[4-(4-fluorophenoxy)phenoxy]ethylcarbamate and 0.3 g of 4-dimethylaminopyridine in 70 ml of 1,2-dichloroethane. The mixture is then stirred for 16 hours at +80° C. After cooling to room temperature, the reaction mixture is washed in succession with a cold 5% solution of sodium hydrogencarbonate, with 0.1N hydrochloric acid and, finally, with water, and dried over sodium sulfate. The 1,2-dichloroethane is completely removed by vacuum distillation. If desired, the crude ethyl N-methoxalyl-2-[4-(4-fluorophenoxy)phenoxy]ethylcarbamate can be purified by chromatography (eluant: 5:1 mixture of n-hexane/diethyl ether); nD20 : 1.5295.

Workup

  1. stirringThe mixture is then stirred for 16 hours at +80° C
  2. washthe reaction mixture is washed in succession with a cold 5% solution of sodium hydrogencarbonate, with 0.1N hydrochloric acid
  3. dry with materialfinally, with water, and dried over sodium sulfate
  4. customThe 1,2-dichloroethane is completely removed by vacuum distillation
  5. customthe crude ethyl N-methoxalyl-2-[4-(4-fluorophenoxy)phenoxy]ethylcarbamate can be purified by chromatography (eluant: 5:1 mixture of n-hexane/diethyl ether)

Sources & evidence

ORD record
ord-a37e9e540a4e4d518b745ce58280c397
Source dataset
uspto-grants-1992_05
Patent number
US05114968

Reaction notes

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