Dibromomethane → Liranaftate

HRID 1717434Notes

Reaction equation

HRID 1717434 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[OH-].[Na+].[C:14](=[S:17])([S-])[NH2:15].[CH3:18][O:19][C:20]1[N:25]=[C:24](NC)[CH:23]=[CH:22][CH:21]=1.[Na+].Br[CH2:30]Br>CN(C=O)C.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[N:25]=[C:24]([N:15]([CH3:30])[C:14](=[S:17])[O:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[CH:1]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 3024DibromomethaneHCID 143055,6,7,8-Tetrahydro-2-naphtholHCID 14798Sodium HydroxideHCID 86761183HCID 86761183, compound

Product 1

HCID 3936LiranaftateYield 58.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5,6,7,8-tetrahydro-2-naphthol (1.48 g, 10 mmol) was dissolved in 10 ml of DMF, after which crushed sodium hydroxide (0.60 g, 15 mmol) was added, then stirred for 10 minutes at room temperature. Next, sodium 6-methoxy-2-methylaminopyridine dithiocarbamate (2.36 g, 10 mmol) was added and the result stirred for 10 minutes. The solution was ice-cooled to 10° C., and dibromomethane (1.74 g, 10 mmol) was added dropwise for 5 minutes, and stirred for 1 hour at room temperature. 100 ml of ethyl acetate were added to the reaction solution to extract, and the organic layer was washed with water. The organic layer was dried with anhydrous magnesium sulfate, then the magnesium sulfate was filtered out. Upon concentrating the filtrate under reduced pressure, an oily residue was obtained. This was purified by column chromatography (hexane:ethyl acetate=20:1), to obtain 1.91 g (yield 58%) of the titled compound in the form of colorless crystals.

Workup

  1. additionwas added
  2. stirringthe result stirred for 10 minutes
  3. temperaturecooled to 10° C.
  4. stirringstirred for 1 hour at room temperature
  5. extractionto extract
  6. washthe organic layer was washed with water
  7. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  8. filtrationthe magnesium sulfate was filtered out
  9. concentrationUpon concentrating the filtrate under reduced pressure
  10. customan oily residue was obtained
  11. customThis was purified by column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-5d150aa3861a4c29b282c8cb29d709eb
Source dataset
uspto-grants-2010_09
Patent number
US07803947B2

Reaction notes

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