Ethyl 3-chloropropionate → 5-Nitro-2-vinylbenzoxazole

HRID 735097Notes

Reaction equation

HRID 735097 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Cl[CH2:13][CH2:14][C:15](OCC)=O.C(=O)([O-])O.[Na+]>>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:15]([CH:14]=[CH2:13])=[N:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 69341Ethyl 3-chloropropionateHCID 516892Sodium BicarbonateHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 688156545-Nitro-2-vinylbenzoxazole

Conditions

Temperature
170 °C

Procedure

A reaction mixture of 1.54 g (10 mmol) of 2-amino-4-nitrophenol, 1.36 g (10 mmol) of ethyl 3-chloropropionate and 20 g polyphosphoric acid is stirred for 2 hours at 170° C. Then the mixture is neutralized by the addition of saturated sodium hydrogen carbonate solution at ambient temperature. The aqueous phase is extracted with dichloromethane. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/ethanol (20:1)). Yield: 0.3 g (15.8% of theory); C9H6N2O3 (M=190.16); calc.: molecular ion peak (M+H)+: 191; found: molecular ion peak (M+H)+: 191; Rf value: 0.8 (silica gel, dichloromethane/ethanol (20:1)).

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customThe purification

Sources & evidence

ORD record
ord-d758b8e950594aeba206156c5408613a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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