Sodium Hydroxide → 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(dibutylaminosulfenyl)-N-methylcarbamate

HRID 434728Notes

Reaction equation

HRID 434728 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]=[N:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[CH3:14].[CH2:19]([N:23]([CH2:30][CH2:31][CH2:32][CH3:33])[S:24][N:25]([C:27](F)=[O:28])[CH3:26])[CH2:20][CH2:21][CH3:22].[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH2:19]([N:23]([CH2:30][CH2:31][CH2:32][CH3:33])[S:24][N:25]([CH3:26])[C:27](=[O:28])[O:13][C:9]1[CH:8]=[C:7]([CH3:14])[C:6]([N:5]=[CH:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[OH:1])=[C:11]([CH3:12])[CH:10]=1)[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 12799219N-(di-n-butylaminosulfenyl)-N-fluorocarbonyl-N-methylamineHCID 1356896104-(2-Hydroxybenzylideneamino)-3,5-dimethylphenol2×

Product 1

HCID 1360029934-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(dibutylaminosulfenyl)-N-methylcarbamate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

In a manner identical to that described in Example II, Part A, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol was prepared. To a 1 liter round bottom flask equipped with a magnetic stirrer was added 9.65 grams (0.040 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol, 10.65 grams (0.045 moles) of N-(di-n-butylaminosulfenyl)-N-fluorocarbonyl-N-methylamine, 400 milliliters of toluene, 100 milliliters of 0.4 molar sodium hydroxide and 10 drops of tricaprylmethylammonium chloride solution. The resulting reaction mixture was stirred continuously for 2 hours at room temperature forming an organic layer. After the stirring period, the organic layer was separated, washed twice with water and twice with a saturated brine solution, dried over magnesium sulfate and concentrated under reduced pressure to give a dark brown oil. Purification of the dark brown oil by column chromatography yielded 2.80 grams (0.0061 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(dibutylaminosulfenyl)-N-methylcarbamate in the form of an amber oil having the following structural formula: ##STR26##

Workup

  1. customwas prepared
  2. customTo a 1 liter round bottom flask equipped with a magnetic stirrer
  3. customThe resulting reaction mixture
  4. customforming an organic layer
  5. customAfter the stirring period, the organic layer was separated
  6. washwashed twice with water and twice with a saturated brine solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a dark brown oil
  10. customPurification of the dark brown oil by column chromatography

Sources & evidence

ORD record
ord-8bb7d2838cba49d2bcbe4fc2d5b7244f
Source dataset
uspto-grants-1983_08
Patent number
US04399148

Reaction notes

Loading…