2-amino-3,6-dichloroPhenol → 2-Chloromethyl-4,7-dichlorobenzoxazole

HRID 1033032Notes

Reaction equation

HRID 1033032 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([Cl: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:4]([Cl:9])=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 103973432-amino-3,6-dichloroPhenolHCID 71342929Ethyl 2-chloroiminoacetate hydrochloride

Product 1

HCID 103992442-Chloromethyl-4,7-dichlorobenzoxazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-3,6-dichlorophenol (23.91 g, 134 mmol) in methylene chloride (270 mL), solid ethyl chloroiminoacetate hydrogen chloride (31.9 g, 202 mmol) was added. The resultant slurry was stirred at room temperature overnight, then filtered through a plug of Celite, and concentrated under reduced pressure (15 torr). The solid residue was subjected to column chromatography on silica gel (elution with chloroform). Collection and concentration of appropriate fractions yielded 26.6 g (86%) of 2-chloromethyl-4,7-dichlorobenzoxazole.

Workup

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

Sources & evidence

ORD record
ord-68abe93ea1c244cd96fc91713bec7e3d
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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