Ammonium Chloride → HCID 178486439, compound

HRID 499029Notes

Reaction equation

HRID 499029 reaction equation
I[C:2]1[N:3]=[C:4]([S:7]([N:10]([CH3:12])[CH3:11])(=[O:9])=[O:8])[NH:5][CH:6]=1.C([Mg]Br)C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[CH3:29])[O:25][CH2:24][CH2:23][C:22]2=[O:30].[Cl-].[NH4+]>C(Cl)Cl>[OH:30][C:22]1([C:2]2[N:3]=[C:4]([S:7]([N:10]([CH3:12])[CH3:11])(=[O:9])=[O:8])[NH:5][CH:6]=2)[C:21]2[C:26](=[CH:27][C:28]([CH3:29])=[C:19]([O:18][CH3:17])[CH:20]=2)[O:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 55297174HCID 55297174, compoundHCID 178418443HCID 178418443, compoundHCID 178486156HCID 178486156, compound

Product 1

HCID 178486439HCID 178486439, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.6 grams (0.016 mole) of [(4-iodoimidazolyl)sulfonyl]dimethylamine (commercially available) in 10 mL of dry methylene chloride was stirred and 5.7 mL (0.018 mole) of ethylmagnesium bromide (3M in diethyl ether) was added. Upon completion of addition, the reaction mixture was stirred during a 2.5 hour period. After this time, 3.0 grams (0.016 mole) of 6-methoxy-7-methylchroman-4-one (ii) (prepared in Step C of Example 5) was added, and the reaction mixture was stirred for an additional 18 hours. After this time, the reaction mixture was poured into 100 mL of an aqueous solution of ammonium chloride and extracted with three 100 mL portions of methylene chloride. The combined extracts were washed with one 50 mL portion of water, and dried with sodium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on Grade II basic alumina (3% water) using a 99:1 mixture of methylene chloride and methanol, respectively, as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 3.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred for an additional 18 hours
  3. extractionextracted with three 100 mL portions of methylene chloride
  4. washThe combined extracts were washed with one 50 mL portion of water
  5. dry with materialdried with sodium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified by column chromatography on Grade II basic alumina (3% water)
  9. additiona 99:1 mixture of methylene chloride and methanol
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd8e5ca34c2040c58ecc05cecad1cbe3
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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