Water → 1-Amino-3-(benzyloxy)-5-chloropyridin-1-ium 2,4,6-trimethylbenzenesulfonate

HRID 2209246Notes

Reaction equation

HRID 2209246 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([CH3:29])[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24]([O:27][NH2:28])(=[O:26])=[O:25].O.CCOCC>ClCCl>[CH3:23][C:18]1[CH:19]=[C:20]([CH3:22])[CH:21]=[C:16]([CH3:29])[C:17]=1[S:24]([O-:27])(=[O:26])=[O:25].[NH2:28][N+:11]1[CH:12]=[C:13]([Cl:15])[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 185161373-(Benzyloxy)-5-chloropyridine

Product 1

HCID 1178429311-Amino-3-(benzyloxy)-5-chloropyridin-1-ium 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(benzyloxy)-5-chloropyridine (4.00 g, 18.2 mmol) in dichloromethane (30.0 mL) was cooled to 0° C. under argon. O-(mesitylsulfonyl)hydroxylamine (5.23 g, 10% water, 21.9 mmol, prepared using a procedure similar to that reported in Org. Proc. Res. Dev. 2009, 13, 263-267) was added slowly and the mixture stirred at 0° C. for 1 h. 100 mL of ether was added, stirred for 5 minutes and filtered. The solids were washed with cold ether and dried on the frit to afford 1-amino-3-(benzyloxy)-5-chloropyridin-1-ium 2,4,6-trimethylbenzenesulfonate.

Workup

  1. addition2009, 13, 263-267) was added slowly
  2. stirringstirred for 5 minutes
  3. filtrationfiltered
  4. washThe solids were washed with cold ether
  5. customdried on the frit

Sources & evidence

ORD record
ord-7897cc15dda945c59747497de3423d57
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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