1-Naphthaleneacetic Acid → N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)-2-(1-naphthyl)acetamide

HRID 443737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443737
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[NH2:33][C:34]([CH:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[OH:38])([CH3:36])[CH3:35]>O1CCCC1>[OH:38][CH:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:34]([NH:33][C:12](=[O:14])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)([CH3:36])[CH3:35]

Komponenten

5

Edukt 3

HCID 68621-Naphthaleneacetic AcidHCID 26760alpha-(1-Amino-1-methylethyl)benzenemethanolHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline

Produkt 1

HCID 12570802N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)-2-(1-naphthyl)acetamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of 74.5 g. (0.4 mole) of 1-naphthyl acetic acid, 111.0 g. (0.45 mole) of EEDQ and 66.0 g. (0.4 mole) of α-(1-amino-1-methylethyl)benzenemethanol in 1 l. tetrahydrofuran is stirred and heated for 2 hours at 65° C. and then allowed to stand for 20 hours at room temperature. THF is evaporated in vacuo, and the residue is taken up with ice and 10% aqueous H2SO4 solution to pH 2. The resulting amide is extracted twice with 750 ml. ethyl acetate. The combined organic extracts are washed with 500 ml. dilute NaHCO3, dried (Na2SO4) and evaporated to dryness in vacuo. The oil is dissolved in 1 l. hot isopropyl ether and on standing at 25° C. gives 101.0 g. (77% yield) of N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)-1-naphthaleneacetamide as an off-white crystalline solid of analytical purity, m.p. 106°-107° C.

Aufarbeitung

  1. customTHF is evaporated in vacuo
  2. extractionThe resulting amide is extracted twice with 750 ml
  3. washThe combined organic extracts are washed with 500 ml
  4. dry with materialdilute NaHCO3, dried (Na2SO4)
  5. customevaporated to dryness in vacuo
  6. dissolutionThe oil is dissolved in 1 l
  7. customon standing at 25° C.
  8. customgives 101.0 g

Quellen und Nachweise

ORD-Eintrag
ord-fab6f957685a4596801c4b256baae3e2
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04261890

Notizen zur Reaktion

Wird geladen…