2-Amino-3,6-dimethylphenol → 2-Chloromethyl-4,7-dimethylbenzoxazole

HRID 1586644Notes

Reaction equation

HRID 1586644 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([NH2:9])[C:3]=1[OH:10].[ClH:11].ClN=CC(O[CH2:18][CH3:19])=O>C(Cl)Cl>[Cl:11][CH2:18][C:19]1[O:10][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[C:5]([CH3:8])[C:4]=2[N:9]=1

Participants

4

Reactant 2

HCID 150363212-Amino-3,6-dimethylphenolHCID 71342929Ethyl 2-chloroiminoacetate hydrochloride

Product 1

HCID 100355622-Chloromethyl-4,7-dimethylbenzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dimethyl-6-aminophenol (0.67 g, 4.9 mmol) in methylene chloride, solid ethyl 2-chloroiminoacetate hydrochloride (0.85 g, 4.9 mmol) was added. The resultant slurry was stirred at room temperature for 18 hours, then filtered through a plug of diatomaceous earth and concentrated under reduced pressure (15 torr). The solid residue was subjected to column chromatography on silica gel (50 g, eluted with 1% methanol in chloroform). Collection and concentration of appropriate fractions yielded the title benzoxazole.

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. concentrationconcentrated under reduced pressure (15 torr)
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-429dd200801c4093bf5e21bf580b0749
Source dataset
uspto-grants-1993_06
Patent number
US05215900

Reaction notes

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