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

HRID 1783607Notes

Reaction equation

HRID 1783607 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-nitrophenoxymethyl)-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-985532295722483ba0fcf54e9aaada80
Source dataset
uspto-grants-2009_03
Patent number
US07501427B2

Reaction notes

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