2-Chloro-1,1,1-triethoxyethane → 2-(Chloromethyl)-4-nitro-1,3-benzoxazole

HRID 241802Notes

Reaction equation

HRID 241802 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12][CH2:13][C:14](OCC)(OCC)OCC>COCCOCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:12][CH2:13][C:14]1[O:11][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 99907762-(Chloromethyl)-4-nitro-1,3-benzoxazoleYield 17.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8150DiglymeSolvent

Procedure

To a RT solution of 2-amino-3-nitrophenol (14.7 g, 95 mmol, 1.0 equiv) in 2-methoxyethylether (136 mL) was added 2-chloro-1,1,1-triethoxyethane (19.1 g, 97.3 mmol, 1.02 equiv) and p-toluene sulfonic acid hydrate (25 mg, 0.13 mmol, 0.2 equiv). The resulting mixture was heate to reflux overnight. After the reaction was cooled to RT, the solvent was removed in vacuo. The solid was suspended in methanol (40 mL), stirred and filtered to provide the desired product as a red solid (3.61 g). The filtrate provided an additional 9.8 g of the title compound through an additional methanol treatment (13.4 g, 98% combined).

Workup

  1. temperatureto reflux overnight
  2. customthe solvent was removed in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-54bb1950931642cf9b9f9fd11df72e40
Source dataset
uspto-grants-2014_02
Patent number
US08653081B2

Reaction notes

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