Hydrochloric Acid → HCID 22708215, compound

HRID 353181Notes

Reaction equation

HRID 353181 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1)=O.[CH3:20][O:21][CH2:22][CH2:23][NH2:24].C([BH3-])#N.[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO.C(O)(=O)C>[CH3:20][O:21][CH2:22][CH2:23][NH:24][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 80182-MethoxyethylamineHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 22708158HCID 22708158, compound

Product 1

HCID 22708215HCID 22708215, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

7.9 g of 1,1-dimethylethyl 2-[(4-formylphenyl)thio]-2-methyl-propanoate and 4.23 g of methoxyethylamine are initially charged in 100 ml of methanol and admixed with 19 ml of acetic acid. The mixture is stirred at RT for 15 min, boiled briefly and then, at 0° C., admixed a little at a time with 8.9 g of sodium cyanoborohydride. The mixture is stirred at room temperature overnight and then admixed with 1 N HCl and stirred for 30 min. The mixture is then made basic using sodium carbonate solution and extracted 2× with ethyl acetate. The organic phase is washed with sat. sodium chloride solution and dried over magnesium sulphate. Concentration and chromatographic purification give 5.6 g (58%) of a colourless oil.

Workup

  1. customat 0° C.
  2. stirringThe mixture is stirred at room temperature overnight
  3. stirringstirred for 30 min
  4. extractionextracted 2× with ethyl acetate
  5. washThe organic phase is washed with sat. sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationConcentration and chromatographic purification

Sources & evidence

ORD record
ord-4440278ca4e74df2bfa44b99cff22335
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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