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

HRID 396281Notes

Reaction equation

HRID 396281 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[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=O)=[N+]=[N-].C[N:26](C)[CH:27]=[O:28]>>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:27]([NH:26][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[O:28])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 5110493Pyridine-2-carbonyl azideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9862893N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(pyridin-2-yl)ureaYield 62%

Procedure

Under Argon, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (300 mg, 1.35 mmol) and 2-(azidocarbonyl)-pyridine (400 mg, 2.70 mmol) in 5 mL of N,N-dimethyl-formamide was heated to 80° C. for 2 hours. The mixture was kept at room temperature for another 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 (287 mg, 62%). LC-MS (m/z) 343.0 (M+).

Workup

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

Sources & evidence

ORD record
ord-285445673ec9445b96c50496387ca86b
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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