Dimethylformamide → HCID 23042161, compound

HRID 2166104Notes

Reaction equation

HRID 2166104 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:20][C:21]1[N:22]=[C:23]([CH3:26])[S:24][CH:25]=1.CN(C)C=[O:30]>>[CH3:26][C:23]1[S:24][CH:25]=[C:21]([CH2:20][O:30][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:22]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 132544-PhenoxyphenolHCID 24758Sodium hydrideHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 23042161HCID 23042161, compound

Conditions

Temperature
80 °C

Procedure

A solution of 8.83 g of 4-phenoxyphenol in 15 ml of absolute dimethylformamide is dripped into 1.5 g of 80% strength sodium hydride in 15 ml of absolute dimethylformamide. Upon completion of hydrogen evolution, 7.0 g of 4-chloromethyl-2-methylthiazole is dripped in and the mixture stirred for 3 hours at 80° C. After the solvent has been removed, the residue is slurried with 200 ml of water and extracted 3 times, each time with 50 ml of ether. After drying over sodium sulfate and removal of the solvent, the crude product is recrystallized from cyclohexane/methyl tert-butyl ether (20:1). There is obtained 6.5 g of 2-methyl-4-[(phenoxyphenoxy)-methyl]-thiazole; m.p.: 70°-73° C.

Workup

  1. customAfter the solvent has been removed
  2. extractionextracted 3 times
  3. dry with materialAfter drying over sodium sulfate and removal of the solvent
  4. customthe crude product is recrystallized from cyclohexane/methyl tert-butyl ether (20:1)

Sources & evidence

ORD record
ord-d07dad5aebbc46e68a843dff4c0355e6
Source dataset
uspto-grants-1990_07
Patent number
US04943584

Reaction notes

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