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

HRID 372344Notes

Reaction equation

HRID 372344 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 5.25g (0.025 mole) of (2,4-dichlorophenoxy)acetaldehyde and 5.0g (0.055 mole) of thioglycolamide in 100 ml of anhydrous ether was added 14.2g (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 1.4g 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-3f8a4448b3094ec4859c52174c3695e1
Source dataset
uspto-grants-1978_05
Patent number
US04090861

Reaction notes

Loading…