p-Toluenesulfonic acid → HCID 21422793, compound

HRID 259055Notes

Reaction equation

HRID 259055 reaction equation
C([O-])([O-])[O:2][CH2:3][CH3:4].[C:7]1(C)C=CC(S(O)(=O)=O)=C[CH:8]=1.[CH2:18]([NH:22][C:23]([O:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=1)[NH:29][C:30](=[O:35])[CH2:31][C:32](=[O:34])[CH3:33])=[O:24])[CH2:19][CH2:20][CH3:21].N1C2C(=CC=CC=2)C=CC=1>CO>[CH2:18]([NH:22][C:23]([O:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=1)[NH:29][C:30](=[O:35])[CH2:31][C:32]([O:2][CH2:3][CH3:4])([O:34][CH2:7][CH3:8])[CH3:33])=[O:24])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7047QuinolineHCID 21422770HCID 21422770, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 21422793HCID 21422793, compoundYield 939.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

52 g of ethyl orthoformate and 1 g of p-toluene sulfonic acid were added to a solution of 59 g of the product of Step A in 180 ml of methanol and the mixture was stirred at room temperature for 7 hours. The mixture was then allowed to stand for 18 hours and 1 ml of quinoline was added thereto. The solvent was evaporated and the residue was chromatographed over silica gel. Elution with an 8-2 methylene chloride-acetone mixture gave 20 g of m-(n-butylcarbamoyloxy)-3,3-diethoxy-butyranilide melting at 130°C.

Workup

  1. waitto stand for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed over silica gel
  4. washElution with an 8-2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-dadc98be2edd411b80bceba91e014397
Source dataset
uspto-grants-1977_07
Patent number
US04036633

Reaction notes

Loading…