Hydrochloric Acid → Methyl [1-(2-((N,N-diphenylamino)carbamoyl)-1E-ethylidene)-1,2,3,4-tetrahydronaphthalen-5-yl]oxyacetate

HRID 234719

Reaktionsgleichung

Reaktionsgleichung von HRID 234719
[C:1](/[CH:4]=[CH:5]/[CH:6]1[C:15]2[C:10](=[C:11]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)([OH:3])=O.Cl.[C:23]1([N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[C:23]1([N:29]([NH:30][C:1]([CH2:4]/[CH:5]=[C:6]2\[CH2:7][CH2:8][CH2:9][C:10]3[C:15]\2=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:3])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 86750227Methyl [1-(2E-carboxyvinyl)-1,2,3,4-tetrahydronaphthalen-5-yl]oxyacetate

Produkt 1

HCID 86750228Methyl [1-(2-((N,N-diphenylamino)carbamoyl)-1E-ethylidene)-1,2,3,4-tetrahydronaphthalen-5-yl]oxyacetateAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the carboxylic acid (prepared in reference example 5, 150 mg), 2-chloro-N-methylpyridinum iodide (197 mg). 1,1-diphenylhydrazine hydrochloride (147 mg) and triethylamine (0.216 ml) in methylene chloride (6 ml) was stirred overnight at room temperature. The mixture was poured into 1N hydrochloric acid, and extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue was crystallized from crystallized ethyl acetate to give the title compound (as pale yellow powder; 167 mg) having the following physical data.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was crystallized
  6. customfrom crystallized ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0ffa1781a30545b6a46a0fe793fac147
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596009

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