Benzene → HCID 57139878, compound

HRID 2259724Notes

Reaction equation

HRID 2259724 reaction equation
[C:1]([C:9]1[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH2:15][C:16]([OH:18])=O)[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C1C=CC=CC=1.[NH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1>O1CCCC1.O>[C:1]([C:9]1[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH2:15][C:16]([NH:32][CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=2)=[O:18])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 22810533,4-DimethoxybenzenepropanamineHCID 15634750HCID 15634750, compound

Product 1

HCID 57139878HCID 57139878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.028 mole of 3-benzoyl-2-nitrobenzeneacetic acid, 50 mL of thionyl chloride and 50 mL of benzene is heated at reflux. The dark solution is concentrated under vacuum. The residue is diluted with benzene and concentrated under vacuum (twice). A portion of the acid chloride (0.01 3 mole) in tetrahydrofuran is added to a solution of 3-amino (3,4-dimethoxyphenyl)propane (0.015 mole). The mixture is stirred at room temperature and then added to 200 mL of cold water. The resulting mixture is extracted with diethyl ether. The combined extracts are washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified using standard procedures to give the product.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. concentrationThe dark solution is concentrated under vacuum
  4. additionThe residue is diluted with benzene
  5. concentrationconcentrated under vacuum (twice)
  6. extractionThe resulting mixture is extracted with diethyl ether
  7. washThe combined extracts are washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified
  11. customto give the product

Sources & evidence

ORD record
ord-59ff462367c444bd9ff8ce202dd99d34
Source dataset
uspto-grants-1995_12
Patent number
US05475034

Reaction notes

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