p-Toluenesulfonic acid → (+/-) trans 1-(4-Benzoylanilino)-2-ethoxycarbonylaminoindane

HRID 965214Notes

Reaction equation

[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].[NH2:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C@@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[NH:8][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:30][CH:29]=1)(=[O:22])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (2.50 g, 0.012 mol) in dry toluene (40 ml) was treated with 4-aminobenzophenone (2.43 g, 0.012 mol) and a catalytic amount of p-toluenesulfonic acid (0.25 ml of an anhydrous 0.1M solution of p-toluenesulfonic acid in benzene). The mixture was heated under nitrogen at 80° C. overnight. The reaction was worked up as described in Preparation 5. Purification on a silica gel column using a graded eluant of 5-40% ethyl acetate in petroleum ether 40/60 afforded the title compound as a yellow foam (3.65 g).

Workup

customas described in Preparation 5
customPurification on a silica gel column

Sources & evidence

ORD record: ord-b15b8f79d71748a089c6da1f3541f00f
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773463

Reaction notes

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