1-Naphthol → 1-[N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyloxy]-napthalene

HRID 1448083Notes

Reaction equation

HRID 1448083 reaction equation
[CH3:1][N:2]([S:6][C:7]([CH3:14])([C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH3:8])[C:3](Cl)=[O:4].[C:15]1([OH:25])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCOCC1.O>[CH3:1][N:2]([S:6][C:7]([CH3:14])([C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH3:8])[C:3]([O:25][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54024146N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl chloride

Product 1

HCID 540653211-[N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyloxy]-napthaleneYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 10.0 g (0.042 m) of N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl chloride and 6.06 g (0.042 m) of 1-naphthol in 75 ml of dioxane was added 4.26 g (0.042 m) of triethylamine. After stirring at room temperature for 17 hours the reaction mixture was diluted with 500 ml of cold water and the product taken into ethyl acetate. The organic phase was washed in turn with 1.0 percent sodium hydroxide and water and then dried over magnesium sulfate. On removal of the solvent it yielded 9.4 g of a residual oil.

Workup

  1. washThe organic phase was washed in turn with 1.0 percent sodium hydroxide and water
  2. dry with materialdried over magnesium sulfate
  3. customOn removal of the solvent it

Sources & evidence

ORD record
ord-6dfc33a7e6d34f0db5d588030af4a4f3
Source dataset
uspto-grants-1979_12
Patent number
US04179514

Reaction notes

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