Dimethylformamide → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(1-phenyl-1H-1,2,3-triazol-5-yl)urea

HRID 396285Notes

Reaction equation

HRID 396285 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(C([C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:22]=[N:21][CH:20]=1)=O)=[N+]=[N-].C[N:31](C)[CH:32]=[O:33]>>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:32]([NH:31][C:19]2[N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:22]=[N:21][CH:20]=2)=[O:33])[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 230036295-(azidocarbonyl)-1-phenyl-1H-1,2,3-triazole

Product 1

HCID 135469500N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(1-phenyl-1H-1,2,3-triazol-5-yl)ureaYield 1.4%

Procedure

Under Ar, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (104 mg, 0.46 mmol) and 5-(azidocarbonyl)-1-phenyl-1H-1,2,3-triazole (100 mg, 0.46 mmol) in 5 mL of N,N-dimethyl-formamide was stirred at room temperature for 3 days. Purification upon Gilson HPLC twice, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (2.7 mg, 1.4%). LC-MS (m/z) 409.9 (M+).

Workup

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

Sources & evidence

ORD record
ord-e1163a6fd94647ad9aa46107457f70d1
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

Loading…