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

HRID 965212Notes

Reaction equation

HRID 965212 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].[Cl:16][C:17]1[CH:18]=[C:19]([SH:24])[CH:20]=[CH:21][C:22]=1[Cl:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1C=CC=CC=1.C(OCC)C>[Cl:16][C:17]1[CH:18]=[C:19]([S:24][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:20]=[CH:21][C:22]=1[Cl:23]

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acid2×HCID 799643,4-DichlorobenzenethiolHCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

Product 1

HCID 53664910(+/-) trans 1-(3,4-Dichlorophenylthio)-2-ethoxycarbonylaminoindaneYield 87.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (0.61 g, 3.0 mmol) in dry toluene (15 ml) was treated with 3,4-dichlorothiophenol (0.59 g, 3.3 mmol) and a catalytic amount of p-toluenesulfonic acid (0.15 ml of an anhydrous 0.1M solution of p-toluenesulfonic acid in benzene). The mixture was heated under nitrogen at 70°-75° C. for 3.5 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 Na2 SO4 and concentrated in vacuo to give a solid (1.0 g). Purification on a silica gel column using CHCl3 as eluant afforded the title compound as a colourless solid (0.81 g).

Workup

  1. temperatureThe mixture was heated under nitrogen at 70°-75° C. for 3.5 h
  2. washwashed with 5% NaOH (3×10 ml)
  3. customThe organic phase was dried over Na2 SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32de7b013ff34f1992f07175f2df1f0b
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

Loading…