Triethylamine → HCID 4136951, compound

HRID 1930281Notes

Reaction equation

HRID 1930281 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 4136951HCID 4136951, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of diketene (0.32 ml, 4.15 mmol) in toluene (2 ml) was added to an 80° C. solution of 4-bromo-2-nitroaniline (900 mg, 4.15 mmol) in toluene (7 ml) and the solution was heated at reflux for 5 h. Triethylamine (0.58 ml, 4.15 mmol) in toluene (2 ml) was added and refluxing was continued for 30 min. The cooled solution was concentrated in vacuo and the crude product purified by column chromatography on silica gel eluting with 2:1 hexane/EtOAc to give the title compound as a yellow solid (920 mg, 74%).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 5 h
  3. temperaturerefluxing
  4. concentrationThe cooled solution was concentrated in vacuo
  5. customthe crude product purified by column chromatography on silica gel eluting with 2:1 hexane/EtOAc

Sources & evidence

ORD record
ord-81b5590cada24dfe9e7793fc03bf3c31
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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