Boron trifluoride etherate → 2-(2,4-Dichlorophenoxymethyl)-4-thiazolidinone

HRID 461286Notes

Reaction equation

HRID 461286 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH:6]=O.[C:13]([NH2:17])(=[O:16])[CH2:14][SH:15].B(F)(F)F.CCOCC>CCOCC>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH:6]1[NH:17][C:13](=[O:16])[CH2:14][S:15]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 129612-MercaptoacetamideHCID 50929372,4-Dichlorophenoxyacetaldehyde

Product 1

HCID 123914942-(2,4-Dichlorophenoxymethyl)-4-thiazolidinoneYield 20.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution containing 5.25 g (0.025 mole) of (2,4-dichlorophenoxy)acetaldehyde and 5.0 g (0.055 mole) of thioglycolamide in 100 ml of anhydrous ether was added 14.2 g (0.10 mole) of boron trifluoride etherate. The resulting solution was stirred at ambient temperature for 6 hours, washed with water, dried (MgSO4), and concentrated to dryness. The residual solid was purified by silica chromatography to give 1.4 g of 2-(2,4-dichlorophenoxymethyl)-4-thiazolidinone as a white crystalline solid melting at 134°-136°.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to dryness
  4. customThe residual solid was purified by silica chromatography

Sources & evidence

ORD record
ord-fc1b8f4a78604274aa0eaca870a4c7f8
Source dataset
uspto-grants-1977_12
Patent number
US04062670

Reaction notes

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