Hydrochloric Acid → HCID 178487676, compound

HRID 643817Notes

Reaction equation

HRID 643817 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1.Cl.[C:18]1([O:24]C2C=CC=CC=2)C=CC=C[CH:19]=1>O1CCOCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:13]([C:18]([OH:24])=[CH:19][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:16]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 7583Diphenyl EtherHCID 108243-Methoxyaniline

Product 1

HCID 178487676HCID 178487676, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred round bottled flask with toluene (100 mL) ethyl benzoyl acetate (18.7 g, 97 mmol) and m-anisidine (12 g, 97 mmol) was added. 4 M HCl in dioxane (0.5 mL) was added and the reaction mixture was refluxed for 6 h (140° C.). The mixture was co-evaporated with toluene. To the crude mixture diphenyl ether (50 mL) was added and the mixture was heated to 280° C. for 2 h. When the theoretical amount ethanol (6 mL) was collected in a Dean Stark trap the heating was stopped and the mixture was cooled to rt. The crude mixture was dissolved in CH2Cl2 (100 mL) and stirred for 30 min. The formed precipitate was filtered off and dried which gave 1 (4.12 g, 16.4 mmol, 17%): pale yellow powder.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated to 280° C. for 2 h
  3. customWhen the theoretical amount ethanol (6 mL) was collected in a Dean Stark trap the heating
  4. temperaturethe mixture was cooled to rt
  5. dissolutionThe crude mixture was dissolved in CH2Cl2 (100 mL)
  6. filtrationThe formed precipitate was filtered off
  7. customdried which

Sources & evidence

ORD record
ord-14e0c64c1b4b4b378b942e6ad658d536
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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