Pyridine →

HRID 1470560Notes

Reaction equation

[S:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.CCN(CC)CC.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[N:24]1[CH:29]=[CH:28][CH:27]=[CH2+:26][CH:25]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([OH:5])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[S:1]1[CH2:4][CH2:3][CH2:2]1

Participants

Reactant 4

HCID 1049Pyridine

HCID 73974-Toluenesulfonyl chloride

HCID 8471Triethylamine

HCID 825323-Thietan-1-ol

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature: -10 °C

Procedure

A solution of thietan-3-ol (450 mg) and Et3N (1 ml) in dichloromethane (3 ml) was added dropwise to over 30 minutes to a solution of p-toluenesulfonyl chloride (1 g) in dichloromethane (3 ml) at −10° C. under argon atmosphere. The yellow solution was stirred at −10° C. for 1 hour then pyridine (1 ml) was added, and the resulting red solution was stirred for 1 hour at −10° C. The precipitated solid was collected by filtration then washed with diethyl ether (3×5 ml) and dried under high vacuum to afford the title compound as a white solid (405 mg). MS (Method A) positive ion mass: 152 (3-pyridinium thietane), negative ion mass: 171 (p-toluenesulfonate). 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

stirringthe resulting red solution was stirred for 1 hour at −10° C
filtrationThe precipitated solid was collected by filtration
washthen washed with diethyl ether (3×5 ml)
customdried under high vacuum

Sources & evidence

ORD record: ord-b94e25c5592a4d2c807bed375e76a5bd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006456B2

Reaction notes

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