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

HRID 2237422Notes

Reaction equation

HRID 2237422 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 heated 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. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-274b1ddc331444c78b474296a8df32bc
Source dataset
uspto-grants-2010_05
Patent number
US07718657B2

Reaction notes

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