2-Mesitylenesulfonyl chloride → HCID 86602685, compound

HRID 133074

Reaction equation

HRID 133074 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([CH:10]1[CH2:12][CH2:11]1)=[O:9].[C:13]1([CH3:26])[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1[S:21]([O:24][NH2:25])(=[O:23])=[O:22].C1(C)C=C(C)C=C(C)C=1S(Cl)(=O)=O>ClCCl>[CH3:20][C:15]1[CH:16]=[C:17]([CH3:19])[CH:18]=[C:13]([CH3:26])[C:14]=1[S:21]([O-:24])(=[O:23])=[O:22].[NH2:25][N+:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([CH:10]1[CH2:11][CH2:12]1)=[O:9]

Participants

5

Reactant 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 4047267N-(Pyrazin-2-YL)cyclopropanecarboxamideHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 86602685HCID 86602685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g (6.13 mmol) of N-pyrazin-2-ylcyclopropanecarboxamide in 10 mL of dichloromethane at 0° C. was added a solution of 1.58 g (7.36 mmol) of O-mesitylenesulfonylhydroxylamine, prepared from mesitylenesulfonyl chloride using a procedure analogous to that described in the literature (Y. Tamura et al., J. Org. Chem., 38: 1239 (1973)). The reaction mixture was allowed to stir at ambient temperature for 1.5 h. The resultant thick yellow mixture was concentrated in vacuo to give the title compound as a yellow solid.

Workup

  1. concentrationThe resultant thick yellow mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-06ee470493f14b238469f78ccd8890e5
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Linked notes

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