Water → HCID 21845561, compound

HRID 1417291Notes

Reaction equation

HRID 1417291 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[S:17][CH:18]=2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10].O.[CH3:31]N(C)C=O>>[OH:3][C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[S:17][CH:18]=2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[O:10][CH3:31]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 21845565HCID 21845565, compound

Product 1

HCID 21845561HCID 21845561, compound

Procedure

50 mg of sodium hydride (60%) were added to a solution of 0.5 g of N-[4-(3,4-dihydroxy-5-nitro-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide in 5 ml of dimethylformamide. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated. The residue was chromatographed on 60 g of Kieselgel 60 with methylene chloride/acetone/formic acid (90:10:2.5) as the eluent. The product-containing fractions were concentrated and, after boiling with 20 ml of diethyl ether, yielded 0.17 g of N-[4-(3-hydroxy-4-methoxy-5-nitro-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as orange colored crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on 60 g of Kieselgel 60 with methylene chloride/acetone/formic acid (90:10:2.5) as the eluent
  5. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-2097e30160154020aedc5efb8468a21a
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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