2,5-Dichlorophenol → HCID 21840897, compound

HRID 1739381Notes

Reaction equation

HRID 1739381 reaction equation
Cl[CH2:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[S:12][CH2:11][N:10]([CH3:13])[CH:9]=1)[O:6][CH3:7].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=1[OH:37]>CCOCC>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=1[O:37][CH2:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[S:12][CH2:11][N:10]([CH3:13])[CH:9]=1)[O:6][CH3:7]

Participants

6

Reactant 4

HCID 662,5-DichlorophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21840893HCID 21840893, compound

Product 1

HCID 21840897HCID 21840897, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To 0.25 g (1 mmol) of 5-(2-chloromethyl-α-methoxybenzyl)-3-methylthiazole, 2 ml of N,N-dimethylformamide, 0.28 g (2 mmol) of potassium carbonate and 0.33 g (2 mmol) of 2,5-dichlorophenol were added and stirred at 80° C. for 3 hours. After completion of the reaction, 100 ml of ether was added and washed twice with 80 ml of brine. The ether layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) and recrystallized from ether/n-hexane to give 5-[2-(2,5-dichlorophenoxymethyl)-α-methoxybenzyl]-3-methylthiazole (0.28 g, 74.0%) as colorless crystals. mp. 78.5-79.5° C.

Workup

  1. additionwas added
  2. washwashed twice with 80 ml of brine
  3. dry with materialThe ether layer was dried over anhydrous magnesium
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)
  6. customrecrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-1b95abebf30c4598ad75d32fa615d80c
Source dataset
uspto-grants-1999_10
Patent number
US05965740

Reaction notes

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