P-Anisidine → HCID 11755168, compound

HRID 1793498Notes

Reaction equation

HRID 1793498 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][C:10]([O:16][CH2:17][CH2:18][CH2:19]Cl)=[CH:11][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][C:10]([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:11][CH:12]=3)[CH:7]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 22022382HCID 22022382, compound

Product 1

HCID 11755168HCID 11755168, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,7-bis(3-chloropropyloxy)naphthalene (1 gm, 0.003 mole) and p-anisidine (1.17 gm, 0.005 mole) were 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 as solid, m.p. 127° C., (yield 1.34 gm, 89%).

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-20916a283f7b4e35ae8b97c1acc5e84b
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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