4-Nitrobenzenesulfonyl chloride → 4-Nitrobenzenesulfonyl chloride

HRID 1858049Notes

Reaction equation

HRID 1858049 reaction equation
[N-:1]=[N+:2]=[N-:3].[S:4]([C:8]1[CH:16]=[CH:15][C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1)([O-])(=[O:6])=[O:5].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)([O-:19])=[O:18].N1(C2C=CN=CC=2)CCCC1.[N-]=[N+]=[N-].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O>[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:29])(=[O:27])=[O:28])=[CH:22][CH:21]=1)([O-:19])=[O:18].[S:4]([N:1]=[N+:2]=[N-:3])([C:8]1[CH:16]=[CH:15][C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1)(=[O:5])=[O:6]

Participants

9

Reactant 5

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 33557Sodium AzideHCID 33558Azide2×HCID 755674-PyrrolidinopyridineHCID 4215492Nosylate

Product 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 5427784-Nitrobenzenesulfonyl azide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Secondary alcohol 7 was converted to azide 8 through the formation of a secondary nosylate using 4-nitrobenzenesulfonyl chloride and 4-pyrrolidinopyridine in chloroform followed by azide displacement with sodium azide in N,N-dimethylformamide at 50° C. The p-methoxy trityl protecting group was selectively removed using 1% p-toluenesulfonic acid in methylene chloride. Nosylation of the primary alcohol with 4-nitrobenzenesulfonyl chloride and pyridine in chloroform provided azido-nosylate 9.

Workup

  1. customThe p-methoxy trityl protecting group was selectively removed

Sources & evidence

ORD record
ord-56c77319f5ac48d79f7584bb9355f664
Source dataset
uspto-grants-2000_11
Patent number
US06150416

Reaction notes

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