Methyl Ethyl Ketone → O-Naphthalen-2-yl (3-methoxyphenyl)methylcarbamothioate

HRID 1583230Notes

Reaction equation

HRID 1583230 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([CH3:13])[C:10](Cl)=[S:11])[CH:6]=[CH:7][CH:8]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[OH:24].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([CH3:13])[C:10](=[S:11])[O:24][C:15]2[CH:16]=[CH:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 2759692N-(3-methoxyphenyl)-N-methylcarbamothioyl chloride

Product 1

HCID 184882O-Naphthalen-2-yl (3-methoxyphenyl)methylcarbamothioateYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.00 g of N-(3-methoxyphenyl)-N-methylthiocarbamoyl chloride, 1.44 g of β-naphthol and 1.66 g of anhydrous potassium carbonate were added to 50 ml of methyl ethyl ketone and heated to reflux for 15 hours. The reaction mixture was poured into water after it was cooled to room temperature and the products were extracted with benzene. The benzene solution was subsequently washed with water and aqueous saturated sodium chloride solution and then benzene was removed by distillation under reduced pressure after drying over anhydrous Magnesium sulfate. The residue was purified by the column chromatography (eluted with benzene on a silica gel) to give 1.45 g of O-2-naphthyl N-(3-methoxyphenyl)-N-methylthiocarbamate in crystalls (Yield: 45%). A part of the crystals was recrystallized from ethanol. Colorless crystalls having melting point of 93° to 94° C. were obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. extractionthe products were extracted with benzene
  4. washThe benzene solution was subsequently washed with water and aqueous saturated sodium chloride solution
  5. custombenzene was removed by distillation under reduced pressure
  6. dry with materialafter drying over anhydrous Magnesium sulfate
  7. customThe residue was purified by the column chromatography (
  8. washeluted with benzene on a silica gel)

Sources & evidence

ORD record
ord-d6949dcf117b49949f0c6fa219d26a5b
Source dataset
uspto-grants-1985_11
Patent number
US04551169

Reaction notes

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