Methyl iodide → Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]dithiocarbamate

HRID 1597797Notes

Reaction equation

HRID 1597797 reaction equation
[C:1](=[S:3])=[S:2].[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[CH2:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[C:17]([CH3:22])[CH:16]=1.[OH-].[K+].[CH3:25]I>CN(C)C=O.O>[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[CH2:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:1](=[S:3])[S:2][CH3:25])=[C:17]([CH3:22])[CH:16]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 9354004-(Benzo(D)Thiazol-2-Ylmethoxy)-2-Methylaniline

Product 1

HCID 18932149Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]dithiocarbamateYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

0.13 ml of carbon disulfide were added to a stirred solution of 500 mg of 4-(benzothiazol-2-yl)methoxy-2-methylaniline [prepared as described in Example 21(b) below] and 114.5 mg of potassium hydroxide in 6 ml of dimethylformamide and 6 ml of water with cooling in an ice-water bath, and the resulting mixture was stirred for 10 minutes. The temperature of the mixture was then elevated to room temperature and the mixture was stirred for a further 30 minutes at this temperature. The reaction mixture was again cooled in an ice-water bath and 0.15 ml of methyl iodide were added thereto and the resulting mixture stirred at this temperature for 10 minutes. The temperature of the reaction mixture was then elevated to room temperature and the mixture was stirred at this temperature for 2.5 hours. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate to give 458.2 mg (yield 68%) of the title compound as a solid having a melting point of 133°-135° C.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. customwas then elevated to room temperature
  3. stirringthe mixture was stirred for a further 30 minutes at this temperature
  4. temperatureThe reaction mixture was again cooled in an ice-water bath
  5. stirringthe resulting mixture stirred at this temperature for 10 minutes
  6. customwas then elevated to room temperature
  7. stirringthe mixture was stirred at this temperature for 2.5 hours
  8. extractionthe resulting mixture was extracted with ethyl acetate
  9. extractionThe resulting extract
  10. washwas washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was removed by evaporation under reduced pressure
  13. customto give a crude crystalline solid which
  14. customwas purified by column chromatography through silica gel using a 3:1
  15. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-84c4311a368449f1b734512307f18afc
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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