Potassium Hydroxide → HCID 9971689, compound

HRID 2210997

Reaction equation

HRID 2210997 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[S:4]([C:7]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:10]2[N:11]=C(C3C=CC=CC=3)[O:13][C:9]=2[CH:8]=1)(=[O:6])=[O:5])[CH3:2].[OH-].[K+]>C(O)C>[CH2:26]([N:3]([CH2:1][CH3:2])[S:4]([C:7]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:10]([NH2:11])=[C:9]([OH:13])[CH:8]=1)(=[O:6])=[O:5])[CH3:27]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 3715238N,N-Diethyl-2-phenylnaphtho[1,2-d][1,3]oxazole-5-sulfonamide

Product 1

HCID 9971689HCID 9971689, compoundYield 152.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N,N-diethyl-2-phenylnaphth[1,2-d]oxazole-5-sulfonamide (38.1 g, 100 mmol), 20% KOH (140 ml) and ethanol (180 ml) was refluxed for 2 h under nitrogen and the product was extracted with ethyl acetate (3×500 ml). The combined extracts were dried over anhydrous sodium sulfate and the solvent evaporated to give 45 g crude N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide as a black sticky oil (50% pure by NMR). An analytical sample was prepared by column chromatography (chloroform) to give pure N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide as a glassy material which upon titration with ether gave a black solid, m.p. 120°-122° C.

Workup

  1. temperaturewas refluxed for 2 h under nitrogen
  2. extractionthe product was extracted with ethyl acetate (3×500 ml)
  3. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-9ff904c099d440bd84766c45ba7cb6cc
Source dataset
uspto-grants-1995_10
Patent number
US05461155

Linked notes

Loading…