p-Toluenesulfonic acid → HCID 22997275, compound

HRID 1166051Notes

Reaction equation

HRID 1166051 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][O:16]C3CCCCO3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:23]([O:25][CH2:26][CH3:27])=[O:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22997274HCID 22997274, compound

Product 1

HCID 22997275HCID 22997275, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(3,4-dichlorobenzyl)-4-(2-tetrahydropyranyloxy)methylindole-2-carboxylate (4.38 g) and p-toluenesulphonic acid (100 mg) in ethanol (100 ml) was stirred at ambient temperature for 3 hours, then concentrated in vacuo and the residue dissolved in ethyl acetate (100 ml), washed with water (100 ml), dried (MgSO4) and concentrated to give the product as an off-white solid (3.22 g, 90%); NMR δ(CD3SOCD3) 1.25 (t, 3H), 4.25 (q, 2H). 4.80 (d, 2H), 5.20 (m, 1H), 5.80 (s, 2H), 6.85 (m, 1H) 7.10 (d, 1H), 7.30 (m, 2H), 7.50 (m, 3H, M/z (+) 378.3 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  3. washwashed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-45d9dce0bb1e474c8f6623d73a6b5ac3
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

Loading…