Sulfur trioxide-pyridine → HCID 86591330, compound

HRID 895317Notes

Reaction equation

HRID 895317 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:9][C:10]1[C:11]2[C:16]([C:17]([CH2:24][OH:25])=[C:18]3[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:8])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)=O.N1C=CC=CC=1>CS(C)=O.CN(C)C>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:9][C:10]1[C:11]2[C:16]([C:17]([CH:24]=[O:25])=[C:18]3[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168533Sulfur trioxide-pyridineHCID 86591329HCID 86591329, compound

Product 1

HCID 86591330HCID 86591330, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 1146TrimethylamineSolvent

Procedure

Compound 3 (2.30 g, 6.55 mmol) was dissolved in the mixture of dry DMSO (20 mL) and trimethylamine (20 mL). To the solution thus prepared was added the solution of pyridine sulfur trioxide (7.30 g, 45.9 mmol) dissolved in dry DMSO (20 mL) over a period of 30 min. The reaction mixture was stirred at room temperature under nitrogen for 30 min, and then poured into ice-water (300 mL), extracted with ethyl acetate (3×100 mL), dried over MgSO4. Solvent evaporation gave a yellow solid (2.30 g, 100%), without further purification. 1H NMR (CDCl3) δ 11.51 (s, 1H), 8.90 (d, J=8.5 Hz, 2H), 8.51 (d, J=8.5 Hz, 2H), 7.70-7.61 (m, 4H), 5.56 (s, 2H), 2.48 (s, 3H), 1.56 (s, 9H).

Workup

  1. customTo the solution thus prepared
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialdried over MgSO4
  4. customSolvent evaporation

Sources & evidence

ORD record
ord-b9f025fdb322496a97169fc7640e580c
Source dataset
uspto-grants-2005_07
Patent number
US06916660B2

Reaction notes

Loading…