p-Toluenesulfonic acid → HCID 21422772, compound

HRID 259056Notes

Reaction equation

HRID 259056 reaction equation
[CH2:1]([NH:5][C:6]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[NH:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16])=[O:7])[CH2:2][CH2:3][CH3:4].[CH:22]([O-])([O-])[O:23]C.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1.N1C2C(=CC=CC=2)C=CC=1>CO>[CH2:1]([NH:5][C:6]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[NH:12][C:13](=[O:18])[CH2:14][C:15]([O:23][CH3:22])([O:17][CH3:27])[CH3:16])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7047QuinolineHCID 21422770HCID 21422770, compoundHCID 53629101Methylorthoformate

Product 1

HCID 21422772HCID 21422772, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 23.5 g of m-(n-butylcarbamoyloxy)-acetylacetanilide 15 g of methyl orthoformate, 75 ml of methanol and 0.5 g of p-toluene sulfonic acid was stirred for 24 hours and 1 ml of quinoline was then added. The solvent was evaporated and the residue was chromatographed over silica. Elution with an 8-2 methylene chloride-acetone mixture yielded 20 g of m-(n-butylcarbamoyloxy)-3,3-dimethoxy-butyranilide melting at 114°C. STEP B: m-(n-butylcarbamoyloxy)-3-methoxy-crotonanilide

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed over silica
  3. washElution with an 8-2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-f8f95645f26c4717a91ccde347cc68af
Source dataset
uspto-grants-1977_07
Patent number
US04036633

Reaction notes

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