Potassium Hydroxide → methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

HRID 1597809Notes

Reaction equation

HRID 1597809 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=1.Cl[CH2:17][C:18]1[S:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1>O.CN(C)C=O>[S:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[CH2:17][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 3049782-(Chloromethyl)benzothiazoleHCID 18932138methyl N-(4-hydroxy-2-methylphenyl)carbamate

Product 1

HCID 18932257methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamateYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.6 g of potassium hydroxide in 10 ml of water was added to a solution of 10.0 g of methyl N-(4-hydroxy-2-methylphenyl)carbamate [prepared as described in Example 15(a) above] in 30 ml of dimethylformamide and 6 ml of water cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 20 minutes, and then a solution of 10.0 g of 2-chloromethylbenzothiazole in 25 ml of dimethylformamide was added to the reaction mixture. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 1 hour, at the end of which time the temperature was elevated further to 60° C. and the reaction mixture stirred for a further 2 hours. The reaction mixture was then poured into water to give a crystalline precipitate which was washed with water and further washed with diethyl ether and then recrystallised from ethyl acetate to give 10.5 g (yield 59%) of the title compound as a crystalline solid having a melting point of 147° to 149° C. The proton nuclear magnetic resonance spectrum was identical to that for the title compound of Example 21.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 1 hour, at the end of which time the temperature
  4. customwas elevated further to 60° C.
  5. stirringthe reaction mixture stirred for a further 2 hours
  6. customto give a crystalline precipitate which
  7. washwas washed with water
  8. washfurther washed with diethyl ether
  9. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-4fa6a6d4493b4ecfb5d196fa486137ae
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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