Hydrochloric Acid → HCID 136364246, compound

HRID 428334Notes

Reaction equation

HRID 428334 reaction equation
[OH-].[K+].[CH:3]([N:6]([CH:44]([CH3:46])[CH3:45])[C:7](=[O:43])[CH:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[N:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([O:31]S(C2C=CC(C)=CC=2)(=O)=O)=[C:26]([CH3:42])[CH:25]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])[CH3:4].Cl>C(O)C>[CH:44]([N:6]([CH:3]([CH3:5])[CH3:4])[C:7](=[O:43])[CH:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[N:23][C:24]1[CH:25]=[C:26]([CH3:42])[C:27]([OH:31])=[C:28]([CH3:30])[CH:29]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54301040HCID 54301040, compound

Product 1

HCID 136364246HCID 136364246, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of potassium hydroxide (10.3 mL, 6 M) and N,N-diisopropyl-3-[2-(3,5-dimethyl-4-tosyloxyphenylazo)phenyl]-3-phenylpropenamide (3.5 g, 5.74 mmol) in ethanol (110 mL) was refluxed for 1 h. The mixture was acidified with hydrochloric acid (conc.) and the solvent evaporated. The residue was partioned between toluene and water. The organic layer was dried (MgSO4) and the solvent evaporated. The crude residue was chromatographed on silica (toluene-ethyl acetate 9:2). Yield 1.3 g (50%). 1H NNR (CDCl3) δ0.71 (d, 3H), 0.80 (br, 3H), 1.27 (d, 3H), 1.40 (d, 3H), 2.20 (s, 3H), 2.23 (s, 3H), 3.25 (m, 1H), 4.35 (m, 1H), 5.52 (brd, 1H), 6.05 and 6.60 (s, 1H), 7.00-7.80 (m, 11H).

Workup

  1. customthe solvent evaporated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent evaporated
  4. customThe crude residue was chromatographed on silica (toluene-ethyl acetate 9:2)

Sources & evidence

ORD record
ord-eefb3e2d0d404da19148e7b13e492eb8
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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