O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → HCID 178425979, compound

HRID 868949Notes

Reaction equation

HRID 868949 reaction equation
[CH3:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1.[C:10]1([CH3:23])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[S:18]([O:21][NH2:22])(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][C:12]1[CH:13]=[C:14]([CH3:16])[CH:15]=[C:10]([CH3:23])[C:11]=1[S:18]([O-:21])(=[O:20])=[O:19].[NH2:22][N:4]1[C:5]([CH3:8])=[CH:6][N:7]=[C:2]([CH3:1])[C:3]1=[NH2+:9]

Participants

4

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 132615003,6-Dimethylpyrazin-2-amine

Product 1

HCID 178425979HCID 178425979, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3,6-dimethylpyrazin-2-amine (1.23 g, 10 mmol) in DCM (20 mL) was cooled to 0° C. and a solution of O-(mesitylsulfonyl)hydroxylamine (4.3 g, 20 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature, stirred for 3 h and then filtered. The solid collected was washed with DCM (50 mL) to give 1-amino-3,6-dimethylpyrazin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate as a brown solid (2.0 g). MS (ESI): m/z 139 [M-199]+.

Workup

  1. temperatureto warm to room temperature
  2. filtrationfiltered
  3. customThe solid collected
  4. washwas washed with DCM (50 mL)

Sources & evidence

ORD record
ord-4d8274074a3f4d36b6e33a57ac6dfc4a
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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