Dimethylformamide → HCID 23504957, compound

HRID 1884903Notes

Reaction equation

HRID 1884903 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[CH:6][CH:7]=1.[N:14]([C:17]([CH:19]([CH2:21][CH2:22][CH3:23])[CH3:20])=O)=[N+]=[N-].CN(C)[CH:26]=[O:27]>>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:26]([NH:14][CH2:17][CH:19]([CH3:20])[CH2:21][CH2:22][CH3:23])=[O:27])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamideHCID 235049582-Azidocarbonylpentane

Product 1

HCID 23504957HCID 23504957, compoundYield 2%

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (175 mg, 0.78 mmol) and the crude 2-azidocarbonyl pentane in 2 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 hours. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (5 mg, 2%). LC-MS (m/z) 336.2 (M+).

Workup

  1. customPurification upon Gilson HPLC
  2. washeluting with acetonitrile/water (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-fd3e6bc89dfb483d925159286336f051
Source dataset
uspto-grants-2004_07
Patent number
US06767922B2

Reaction notes

Loading…