p-Toluenesulfonic acid → (+/-) trans 1-(3,4-Dichloroanilino)-2-ethoxycarbonylaminoindane

HRID 965215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965215
[CH2:1]([O:3][C:4]1[O:5][C@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[N:8]=1)[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Cl:24])[NH2:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Cl:24])[NH:20][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:7]1[NH:8][C:4]([O:3][CH2:1][CH3:2])=[O:5]

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acid2×HCID 72573,4-DichloroanilineHCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

Produkt 1

HCID 53724852(+/-) trans 1-(3,4-Dichloroanilino)-2-ethoxycarbonylaminoindaneAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (1.0 g, 0.005 mol) in dry toluene (20 ml) was treated with 3,4-dichloroaniline (0.81 g, 0.005 mol) and a catalytic amount of p-toluenesulfonic acid (5 ml of an anhydrous 0.1M solution of p-toluenesulfonic acid in benzene). The mixture was heated under nitrogen at 60° C. for 3 h. The reaction was worked up as described in Preparation 5. Purification on a silica gel column using 1% ethanol in chloroform as eluant afforded the title compound as a solid (1.33 g).

Aufarbeitung

  1. customas described in Preparation 5
  2. customPurification on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-845aecd90193438a9509dd5805eb6fa5
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773463

Notizen zur Reaktion

Wird geladen…