Sodium Carbonate → HCID 86646582, compound

HRID 2080552Notes

Reaction equation

HRID 2080552 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][CH2:11][CH2:12][NH2:13])=[CH:5][CH:4]=1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1.S([O-])([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21][NH:13][CH2:12][CH2:11][S:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27640536-Chloropyridine-3-carbaldehydeHCID 4364923HCID 4364923, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86646582HCID 86646582, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under a dry nitrogen atmosphere, a mixture of 8.0 grams (0.041 mole) of 2-[(4methoxyphenyl)-methylthio]ethylamine (known compound), 5.7 grams (0.041 mole) of 6-chloropyridine-3-carbaldehyde and 9.7 grams (0.081 mole) of magnesium sulfate in 160 mL of 1,2-dichloroethane was stirred at ambient temperature for about five hours. Sodium triacetoxyborohydride (12.9 grams, 0.061 mole) was added and the reaction mixture stirred at ambient temperature for about 18 hours. After this time 200 mL of an aqueous 5% sodium carbonate solution was added and the mixture stirred for two hours. The mixture was filtered and the filter cake rinsed with methylene chloride. The filtrate and rinse were combined and extracted with three portions of methylene chloride. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a yellow oil. The oil was subjected to several column chromatography purifications on silica gel, combining the appropriate fractions and concentrating prior to the next purification, eluting with mixtures of methylene chloride and methanol. The third chromatography purification provided 9.39 grams of [(6-chloro(3-pyridyl))methyl]{2-[(4-methoxyphenyl)methylthio]ethyl}amine as an oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for about 18 hours
  2. stirringthe mixture stirred for two hours
  3. filtrationThe mixture was filtered
  4. washthe filter cake rinsed with methylene chloride
  5. washThe filtrate and rinse
  6. extractionextracted with three portions of methylene chloride
  7. dry with materialThe combined extracts were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a yellow oil
  10. concentrationconcentrating
  11. customto the next purification
  12. washeluting with mixtures of methylene chloride and methanol
  13. customThe third chromatography purification

Sources & evidence

ORD record
ord-636c38ceb5f141cf928acd3382640c98
Source dataset
uspto-grants-2011_04
Patent number
US07932393B2

Reaction notes

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