Water → 2-((2-Chloro-4-nitrophenoxy)methyl)thiazole

HRID 732277Notes

Reaction equation

HRID 732277 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][OH:7].[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1F.O>CN(C=O)C>[Cl:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[O:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 27952131,3-Thiazol-2-ylmethanol

Product 1

HCID 534010062-((2-Chloro-4-nitrophenoxy)methyl)thiazoleYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Chloro-4-nitro-phenoxymethyl) thiazole is prepared by adding thiazol-2-yl-methanol (2.74 g, 23.76 mmol) to a slurry of sodium hydride (1.21 g of a 60% dispersion in oil, 30.2 mmol) in DMF (10 ml) at 0° C. After several minutes, 2-chloro-1-fluoro-4-nitro-benzene (3.79 g, 21.60 mmol) is added and the reaction mixture warmed to room temperature. The reaction mixture is stirred at room temperature for 3 h, and 60° C. for 16 h. After cooling to room temperature, the reaction mixture is poured into 200 ml water. The resulting precipitate is collected by filtration, washed with water, and dried in vacuo to give 2-(2-chloro-4-nitro-phenoxymethyl)-thiazole (5.80 g, 99%) which is used without further purification.

Workup

  1. custom2-(2-Chloro-4-nitro-phenoxymethyl) thiazole is prepared
  2. waitAfter several minutes
  3. wait60° C. for 16 h
  4. temperatureAfter cooling to room temperature
  5. filtrationThe resulting precipitate is collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9f788b13402c4f828fb8c21313113e9f
Source dataset
uspto-grants-2009_09
Patent number
US07585975B2

Reaction notes

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