2-Amino-4-bromopyridine → 1,2-Diamino-4-bromo-pyridinium 2,4,6-trimethyl-benzenesulfonate

HRID 1802136Notes

Reaction equation

HRID 1802136 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].[Br:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=1>ClCCl.C(OCC)C>[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]([Br:15])=[CH:17][C:18]=1[NH2:22]

Participants

5

Reactant 2

HCID 6932822-Amino-4-bromopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 866660161,2-Diamino-4-bromo-pyridinium 2,4,6-trimethyl-benzenesulfonateYield 82.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled suspension of O-(mesitylsulfonyl)hydroxylamine (11.22 g, 52.1 mmol, 1 eq) in dichloromethane (130 ml) is portionwise added 4-bromopyridin-2-amine (9.3 g, 52.1 mmol, 1 eq.) (exothermic reaction, some cooling is needed) giving a white suspension. After 1 hour the white suspension is diluted with diethyl ether (120 ml). The white solid is collected by filtration, washed with diethyl ether and dried affording 1,2-diamino-4-bromo-pyridinium 2,4,6-trimethyl-benzenesulfonate (16.74 g, 82.7%) as white crystals. mp.: 176-180° C. MS: m/z=188.2, 190.2 (M+H+).

Workup

  1. customexothermic reaction
  2. customgiving a white suspension
  3. filtrationThe white solid is collected by filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-7108a5e7f53c4a7caa056221d4f00642
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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