p-Aminoacetophenone → HCID 178467002, compound

HRID 1702594Notes

Reaction equation

HRID 1702594 reaction equation
NC1C=CC(C(=O)C)=CC=1.Cl.C(OC(CC(OCC)=O)=N)C.[NH4+].[Cl-].[CH2:25]([O:27][C:28]([CH2:39][C:40]([O:42]CC)=O)=[N:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][CH:31]=1)[CH3:26].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:36]([C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[N:29]=[C:28]([O:27][CH2:25][CH3:26])[CH:39]=[C:40]2[OH:42])(=[O:38])[CH3:37]

Participants

7

Reactant 5

HCID 7468p-AminoacetophenoneHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 25517Ammonium ChlorideHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 54252995HCID 54252995, compound

Product 1

HCID 178467002HCID 178467002, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 14.5 gm. (0.107 moles) of p-aminoacetophenone and 19.0 gm. (0.097 moles) of ethyl (1-ethoxyformimidoyl)acetate hydrochloride (Chem. Ber., 100, 1428 (1967)) in 500 ml. of dry CH2Cl2 was stirred at 22° C. for 18 hours. The reaction, containing a precipitate of NH4Cl, was washed successively with ice cold aqueous solutions of 1 N HCl (2×100 ml), in Na2CO3 (2×100 ml) and saturated NaCl, and dried over Na.SO4. Filtration and evaporation yielded 20 gm. of crude ethyl [1-ethoxy(N-p-acetylphenyl)formimidoyl]acetate. This crude material was stirred and heated at 250° in 150 ml. of Dowtherm A for 30 minutes. Cooling dilution with 400 ml. of 1:1 ether-hexane and filtration of the precipitate yielded 12 gm. of the title compound. By base extraction of the filtrate and acidification, a further 2.5 gm. of product was obtained, mp. 210°-219° C. (65% yield).

Workup

  1. additionA mixture of 14.5 gm
  2. customThe reaction
  3. washwas washed successively with ice cold aqueous solutions of 1 N HCl (2×100 ml), in Na2CO3 (2×100 ml)
  4. dry with materialsaturated NaCl, and dried over Na
  5. filtrationFiltration and evaporation
  6. customyielded 20 gm
  7. temperatureheated at 250° in 150 ml
  8. temperatureCooling dilution with 400 ml
  9. filtrationof 1:1 ether-hexane and filtration of the precipitate
  10. customyielded 12 gm

Sources & evidence

ORD record
ord-28ff520267f348f393652de360b92112
Source dataset
uspto-grants-1982_09
Patent number
US04348398

Reaction notes

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