Diethyl Ether → HCID 12291499, compound

HRID 1500743Notes

Reaction equation

HRID 1500743 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[C:15](#[N:22])[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C(OCC)C>ClCCl>[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:19]1[CH:20]=[CH:21][C:16]([C:15]#[N:22])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 75064-CyanopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 12291499HCID 12291499, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of O-(mesitylsulfonyl)hydroxylamine (prepared as described in Synthesis, 1977, 1; 2.17 g, 10.1 mmol) in anhydrous dichloromethane (21 mL) was added dropwise to a stirred solution of isonicotinonitrile (1.05 g, 10.1 mmol) in anhydrous dichloromethane (10 mL) at 0° C. and the mixture was stirred at ambient temperature for 1 hour and 30 minutes. Diethyl ether was then added to the mixture and the precipitate that formed was collected by filtration, washed with diethyl ether and dried in vacuo to give the title compound (3.03 g, 94%) as a white solid.

Workup

  1. customthe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3cb60833765143c297f7430e4b8429d2
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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