2-Benzylaniline → (+/-) trans 1-(2-Benzylanilino)-2-ethoxycarbonylaminoindane

HRID 965208Notes

Reaction equation

HRID 965208 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].[CH2:16]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.C(OCC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:16]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][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])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 1198052-BenzylanilineHCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

Product 1

HCID 54044406(+/-) trans 1-(2-Benzylanilino)-2-ethoxycarbonylaminoindaneYield 87.2%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (2.0 g, 0.01 mol) in dry toluene (15 ml) was treated with 2-benzylaniline (1.83 g, 0.01 mol) and a catalytic amount of p-toluenesulfonic acid monohydrate (50 mg), and the mixture was heated at 60° C. for 1.5 h. The reaction was diluted with diethyl ether, and washed with water followed by brine. The organic phase was dried over Na2SO4 and concentrated in vacuo to give the title compound as a brown foam (3.37 g) which was used in the next stage without purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57700ea61c684b17a676431f4577f92a
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

Loading…