Dimethylformamide → HCID 10154688, compound

HRID 396293Notes

Reaction equation

HRID 396293 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:20]=[N:21][O:22][C:23]=1[CH3:24])=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:20]=[N:21][O:22][C:23]=2[CH3:24])=[O:28])[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 23003636HCID 23003636, compound

Product 1

HCID 10154688HCID 10154688, compoundYield 23%

Procedure

Under Ar, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (238 mg, 1.07 mmol) and the crude material of 4-(azidocarbonyl)-5-methylisooxazole in 5 mL of N,N-dimethyl-formamide was stirred for 18 hours at room temperature. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (86 mg, 23%). LC-MS (m/z) 347.0 (M+).

Workup

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

Sources & evidence

ORD record
ord-87d5bd46a6024dfea2d044739a191cf7
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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