3-Methyl-4-nitrophenol → 2-[(3-Methyl-4-nitrophenoxy)methyl]-1,3-benzothiazole

HRID 1597806Notes

Reaction equation

HRID 1597806 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl[CH2:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1>CN(C)C=O>[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[CH2:15][O:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH3:3])[CH:5]=1

Participants

5

Reactant 3

HCID 174123-Methyl-4-nitrophenolHCID 24758Sodium hydrideHCID 3049782-(Chloromethyl)benzothiazole

Product 1

HCID 9353992-[(3-Methyl-4-nitrophenoxy)methyl]-1,3-benzothiazoleYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

23.0 g of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 80.0 g of 3-methyl-4-nitrophenol in 700 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 20 minutes, at the end of which time a solution of 95.9 g of 2-chloromethylbenzothiazole in 50 ml of dimethylformamide was added to the reaction mixture. The temperature of the resulting mixture was elevated to 80° C. and the mixture was then stirred for 2 hours. At the end of this time, the reaction mixture was poured into ice-water and the precipitated crystalline solid was washed with water. The crude crystalline solid thus obtained was recrystallised from toluene to give 98.8 g (yield 63%) of the title compound as a solid having a melting point of 145° to 147° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. additionwas added to the reaction mixture
  3. customwas elevated to 80° C.
  4. washthe precipitated crystalline solid was washed with water
  5. customThe crude crystalline solid thus obtained
  6. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-1f987ea09ff840a396ed0644c476e9db
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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