4-Toluenesulfonyl chloride → HCID 18993251, compound

HRID 375641Notes

Reaction equation

HRID 375641 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]=[N+]=[N-])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.BrN1C(=O)CCC1=O.[N-]=[N+]=[N-].[Na+].[CH3:40][N:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42]1>>[CH3:40][N:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]([NH:14][S:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:6][CH:7]=2)(=[O:13])=[O:12])=[CH:42]1

Participants

6

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 117811-MethylindoleHCID 33557Sodium AzideHCID 67184N-bromobutanimideHCID 18993232HCID 18993232, compound

Product 1

HCID 18993251HCID 18993251, compound

Conditions

Temperature
55 °C

Procedure

A mixture of 4-azidomethylphenylsulfonyl azide (2.93 g, 12.3 mmol), prepared by reaction of p-toluenesulfonyl chloride with N-bromosuccinimide followed by sodium azide, and 1-methylindole was heated at 55° C. for 6 hours. Pure 1-methyl-3-[4-(azidomethyl)phenylsulfonylamino]indole was obtained by chromatography on silica gel (1:1 CH2Cl2 /hexanes, then CH2Cl2, then 1.5% methanol/CH2Cl2).

Sources & evidence

ORD record
ord-522686effa564459919e0cddf9448c5c
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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