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

HRID 1958093Notes

Reaction equation

HRID 1958093 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 heat to relflux 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 heat to relflux overnight
  2. customthe solvent was removed in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-90b79fb37f0343b49a88e1e37e8e8b49
Source dataset
uspto-grants-2013_04
Patent number
US08410108B2

Reaction notes

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