Hydrochloric Acid → HCID 53644717, compound

HRID 1005568Notes

Reaction equation

HRID 1005568 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([S:15][CH3:16])=[O:14].CN([CH:25](N(C)C)[O:26][C:27](C)(C)C)C.Cl.C(=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O.CN(C)C=O>[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[CH:25][O:26][CH3:27])[C:13]([S:15][CH3:16])=[O:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 15335113HCID 15335113, compound

Product 1

HCID 53644717HCID 53644717, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2 g (0.00665 mol) of S-methyl 2-(2,5-dimethylphenoxymethyl)-phenylthioacetate and 2 g (0.0115 mol) of bis-(dimethylamino)-tert-butoxymethane are heated to 60° C. for 1 hour. The mixture is then admixed with 6 ml of dimethylformamide and 3 ml of concentrated aqueous hydrochloric acid and heated to 60° C. for a further hour. The reaction mixture is admixed with water and extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The resulting crude intermediate, S-methyl 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2-hydroxymethylidene-thio acetate, is dissolved in 10 ml of dimethylformamide, admixed first with 1.6 g (0.0116 mol) of potassium carbonate and then with 0.8 g (0.00634 mol) of dimethyl sulphate and stirred at 20° C. for 24 hours. The mixture is poured into water and extracted with dichloromethane, the organic phase is dried over sodium sulphate, the solvent is distilled off under reduced pressure and the residue is chromatographed over silica gel using diethyl ether/petroleum ether (1:1). 0.5 g (22.9% of theory) of S-methyl 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2-methoxymethylidene-thioacetate is obtained.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting crude intermediate, S-methyl 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2-hydroxymethylidene-thio acetate, is dissolved in 10 ml of dimethylformamide
  5. extractionextracted with dichloromethane
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-d14e8bf6a25b4e8a89b83e225775df91
Source dataset
uspto-grants-2000_04
Patent number
US06054621

Reaction notes

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