Ammonium Chloride → HCID 58130330, compound

HRID 1515364Notes

Reaction equation

HRID 1515364 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][C:10]=2[CH3:20])=[CH:5][CH:4]=1.C([O-])(O)=[O:22].[Na+].[BH4-].[Na+].[Cl-].[NH4+]>ClC1C=CC=CC=1.CO>[OH:22][CH2:20][C:10]1[S:11][C:12]2[C:17]([C:18](=[O:19])[C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 58130398HCID 58130398, compound

Product 1

HCID 58130330HCID 58130330, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

The compound (1.0 mmol, 282 mg) obtained in (1) above and SeO2 (1.2 mmol, 133 mg) were dissolved in 5 mL of chlorobenzene, and the solution was refluxed for 12 hours under a nitrogen atmosphere. After the disappearance of the starting materials was confirmed by NMR, the temperature of the solution was returned to room temperature, and saturated NaHCO3 was poured thereinto to terminate the reaction. The organic substances were extracted with methylene chloride, the obtained organic layer was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was passed through a silica-gel column, and directly used in the subsequent reaction. The obtained mixture was dissolved in 2 mL of methanol, to which NaBH4 (1.0 mmol, 38 mg) was added; and under a nitrogen atmosphere, the resulting product was stirred at 0° C. for 2 hours. A saturated ammonium chloride solution was added thereto to terminate the reaction. Then, the organic layer extracted with ethyl acetate was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized with hexane/ethyl acetate. Thereby, the title compound (0.41 mmol, 122 mg) was obtained in a two-step yield of 41%.

Workup

  1. temperaturethe solution was refluxed for 12 hours under a nitrogen atmosphere
  2. customwas returned to room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionThe organic substances were extracted with methylene chloride
  6. dry with materialthe obtained organic layer was dried over magnesium sulfate
  7. customthe solvents were evaporated under reduced pressure
  8. customdirectly used in the subsequent reaction
  9. additionwas added
  10. customto terminate
  11. customthe reaction
  12. extractionThen, the organic layer extracted with ethyl acetate
  13. dry with materialwas dried over magnesium sulfate
  14. customthe solvents were evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography
  16. customrecrystallized with hexane/ethyl acetate

Sources & evidence

ORD record
ord-f174dfcd88974b118170fb8c3f59d9a4
Source dataset
uspto-grants-2012_07
Patent number
US08222429B2

Reaction notes

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