Dimethylformamide → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(2-chloro-pyridin-3-yl)urea

HRID 396283Notes

Reaction equation

HRID 396283 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[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=1)=O)=[N+]=[N-].C[N:27](C)[CH:28]=[O:29]>>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:28]([NH:27][C:19]2[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:29])[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 230036353-(Azidocarbonyl)-2-chloropyridine

Product 1

HCID 10177585N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(2-chloro-pyridin-3-yl)ureaYield 18%

Procedure

Under Ar, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (50 mg, 0.22 mmol) and 3-(azidocarbonyl)-2-chloropyridine (123 mg, 0.67 mmol) in 1 mL of N,N-dimethyl-formamide was stirred at room temperature for 3 days. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (15 mg, 18%). LC-MS (m/z) 377.0 (M+).

Workup

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

Sources & evidence

ORD record
ord-4220f4efeaa846c28afe4dd3ae40ae1e
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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