Thiophenol → (+/-) trans 1-(Phenylthio)-2-ethoxycarbonylaminoindane

HRID 965210Notes

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].[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.C(OCC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:16]1([S:22][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:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (1.0 g, 0.005 mol) in dry toluene (5 ml) was treated with thiophenol (0.55 g, 0.005 mol) and a catalytic amount of p-toluenesulfonic acid monohydrate (25 mg). The mixture was heated at 60° C. for 2 h and then at 80° C. for a further 5 h. The reaction was diluted with diethyl ether and washed with 5% NaOH (3×10 ml) followed by water (10 ml) and brine (10 ml). The organic phase was dried over Na2SO4 and concentrated in vacuo to give an oil (1.4 g) which was purified on a silica gel column using CH2Cl2 as eluant. Pooling of fractions containing the major slower running component afforded the title compound as a colourless solid (0.74 g), m.p. 60.5°-62° C. (from n-pentane/diethyl ether).

Workup

washwashed with 5% NaOH (3×10 ml)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1f99f6bc7a1d421798b66d12d2dcb664
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773463

Reaction notes

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