Diethyl Ether → HCID 54130575, compound

HRID 728381Notes

Reaction equation

HRID 728381 reaction equation
[Cl:1][C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11](Cl)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=O.C([SH:21])C.C(=O)([O-])[O-].[K+].[K+].C(O[CH2:31][CH3:32])C>CN(C=O)C>[Cl:1][C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11]([CH2:31][CH3:32])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[S:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 14851234Ethyl 2,4-dichloro-3-(2-methoxyethoxy)benzoate

Product 1

HCID 54130575HCID 54130575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (34 mmole) ethyl 2,4-dichloro-3-(2-methoxyethoxy)benzoate, 10 g (4 eq) ethanethiol and 10 g (2 eq) potassium carbonate in 100 ml DMF was heated (approximately 100° C.) for 2 hours, then let cool overnight. Added 400 ml diethyl ether and washed with 100 ml water (two times), 100 ml 10% HCl and 100 ml 10% NaOH. Dried (MgSO4) and reduced under vacuum. Yield 10 g (31 mmole) of an oil.

Workup

  1. temperaturelet cool overnight
  2. washwashed with 100 ml water (two times), 100 ml 10% HCl and 100 ml 10% NaOH
  3. dry with materialDried (MgSO4)

Sources & evidence

ORD record
ord-5337728f8fc74ed3aadd5c0b1f81c597
Source dataset
uspto-grants-1991_09
Patent number
US05047572

Reaction notes

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