p-Toluenesulfonic acid → HCID 86752855, compound

HRID 965216Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (±) cis-2-ethoxy-3a,4,5,9b-tetrahydronapth[2,1-d]oxazole (1.90 g, 8.76 mmol) in dry toluene (15 ml) was treated with 2-benzylaniline (1.60 g, 8.76 mmol) and a catalytic amount of p-toluenesulfonic acid (0.5 ml of an anhydrous 0.1M solution of p-toluenesulfonic acid in benzene). The mixture was heated at 50° C. for 1.5 h. The reaction was worked up as described in Preparation 5. Trituration with n-pentane afforded the title compound as a pale yellow solid (2.47 g).

Workup

customas described in Preparation 5

Sources & evidence

ORD record: ord-a757ef0f9a9740439b61dc8ae33b50c5
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773463

Reaction notes

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