Ammonium Chloride → HCID 59578632, compound

HRID 2201661Notes

Reaction equation

HRID 2201661 reaction equation
[CH2:1]([Zn]CC)C.[CH2:6]=[C:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:8]1.[Cl-].[NH4+]>C(Cl)Cl>[CH2:1]1[C:7]2([CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:9][CH2:8]2)[CH2:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 44182358HCID 44182358, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59578632HCID 59578632, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethyl zinc (40 mL, 1 M solution in hexane) was slowly added to 300 mL of anhydrous DCM at −78° C. under nitrogen, further dimethyl iodide (15 g, 56 mmol) was added slowly. After 30 minutes, warmed to room temperature and maintained for 30 minutes, cooled with an ice-water bath. Then a solution of Compound 7-2 (2 g, 9.5 mmol) dissolved in 10 mL of methylene chloride was added and reacted overnight. To the reaction mixture was poured 100 mL of saturated aqueous solution of ammonium chloride, and liquid separated, the organic phase was extracted with ethyl acetate (100 mL) twice, the organic phases were combined and dried over anhydrous sodium sulfate. Suction filtered to remove desiccant, and rotary evaporated to remove solvents. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1) to give Compound 7-3 as a white solid (0.8 g, 37.4% yield).

Workup

  1. temperaturemaintained for 30 minutes
  2. temperaturecooled with an ice-water bath
  3. additionwas added
  4. customreacted overnight
  5. customseparated
  6. extractionthe organic phase was extracted with ethyl acetate (100 mL) twice
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationSuction filtered
  9. customto remove desiccant
  10. customrotary evaporated
  11. customto remove solvents
  12. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-45508b7b74ee4fad8e3b6c77ad2ac32c
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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