N-(2,2-dimethoxyethyl)-4-iodobenzamide → 2-(4-Iodophenyl)oxazole

HRID 1046314Notes

Reaction equation

HRID 1046314 reaction equation
CO[CH:3]([O:15]C)[CH2:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[I:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[O:15][CH:3]=[CH:4][N:5]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 10903782N-(2,2-dimethoxyethyl)-4-iodobenzamide

Product 1

HCID 98602582-(4-Iodophenyl)oxazoleYield 82.4%

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Procedure

A solution of N-(2,2-dimethoxyethyl)-4-iodobenzamide (10 g, 30 mmol) in Eaton's reagent (100 mL) was heated at 135° C. for 17 hours. The reaction was allowed to cool and poured into ice water. The brown solid was isolated by filtration. Purification on silica gel eluting with dichloromethane gave 6.7 g of 2-(4-iodophenyl)oxazole, 1H NMR (400 MHz, CDCl3) δ 7.79 (q, 4H), 7.72 (s, 1H), 7.27 (s, 1H).

Workup

  1. temperatureto cool
  2. customThe brown solid was isolated by filtration
  3. customPurification on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-0c6040ce6b17476c89874bc34657db24
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

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