Pyridine →

HRID 1470561Notes

Reaction equation

HRID 1470561 reaction equation
[S:1]1[CH2:4][CH:3](O)[CH2:2]1.CCN(CC)CC.[C:13]1([CH3:33])[CH:18]=[CH:17][C:16]([S:19]([O:22]S(C2C=CC(C)=CC=2)(=O)=O)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)(Cl)Cl.ClCCl>[N:34]1[CH:39]=[CH:38][CH:37]=[CH2+:36][CH:35]=1.[C:13]1([CH3:33])[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[S:1]1[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 825323-Thietan-1-ol

Product 0

No Product data yet.

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of thietan-3-ol (450 mg) and Et3N (1.3 ml) in chloroform (5 ml) was added dropwise to over 30 minutes to a solution of p-toluenesulfonic anhydride (1.63 g) in dichloromethane (10 ml) at −20° C. under argon atmosphere. After 2 hours, pyridine (0.8 ml) was added and the resulting mixture was stirred at room temperature for 2 days. The precipitated solid was collected by filtration (300 mg). 1H-NMR (DMSO, 400 MHz): 2.30 (s, 3H), 3.57 (t, 2H), 4.09 (t, 2H), 6.16 (q, 1H), 7.12 (d, 2H), 7.50 (d, 2H), 8.20 (t, 2H), 8.66 (t, 1H), 9.21 (d, 1H).

Workup

  1. filtrationThe precipitated solid was collected by filtration (300 mg)

Sources & evidence

ORD record
ord-f6282334725840aa94460d01e1cd0494
Source dataset
uspto-grants-2015_04
Patent number
US09006456B2

Reaction notes

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