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

HRID 1589782Notes

Reaction equation

HRID 1589782 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. 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-800e31f3f2fb4da5a0114594802d451a
Source dataset
uspto-grants-1993_04
Patent number
US05200329

Reaction notes

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