P-Anisidine → HCID 10096933, compound

HRID 1793499Notes

Reaction equation

HRID 1793499 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][CH2:18][CH2:19]Cl)[CH:12]=2)[CH:7]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>CS(C)=O>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][CH2:18][CH2:19][NH:29][C:26]4[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)[CH:12]=3)[CH:7]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 85999797HCID 85999797, compound

Product 1

HCID 10096933HCID 10096933, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,6-bis(3-chloropropyloxy)naphthalene(1 gm, 0.003 mole) and p-anisidine(1.17 gm, 0.005 mole) was taken in 60 ml dry DMSO. It was refluxed at 140° C. for 12 hrs. The completion of the reaction was checked by TLC. The reaction mixture was poured into distilled water (80 ml) and extracted with ethyl acetate thrice. The organic layer was separated and concentrated to get oily compound which was further crystallized by benzene hexane to get the desired compound, m.p. 129° C., (yield 1.4 gm, 91%).

Workup

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water (80 ml)
  3. extractionextracted with ethyl acetate thrice
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customto get oily compound which
  7. customwas further crystallized by benzene hexane

Sources & evidence

ORD record
ord-8602afcfcfc34702adeae4b8cb6b6cad
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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