Water → HCID 20393335, compound

HRID 1112496Notes

Reaction equation

HRID 1112496 reaction equation
C1(NS(O)(=O)=O)CCCCC1.[CH2:12]([N:14]([CH2:38][CH3:39])[CH2:15][CH2:16][N:17]([CH3:37])[C:18]([C:20]1N(C)[C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:23]2[C:28]=1[CH:27]=[CH:26][C:25]([Cl:29])=[CH:24]2)=[O:19])[CH3:13].[OH-:40].[NH4+].[OH2:42]>>[CH2:12]([N:14]([CH2:38][CH3:39])[CH2:15][CH2:16][N:17]([CH3:37])[C:18](=[O:19])[C:20]([C:28]1[CH:27]=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=1[C:22](=[O:42])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:40])[CH3:13]

Participants

4

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 20393357HCID 20393357, compound

Product 1

HCID 20393335HCID 20393335, compound

Conditions

Temperature
80 °C

Procedure

A solution of 34.6 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid[ 2-(diethylamino)ethyl]-methylamide cyclohexanesulfamate in 400 ml. of water is treated with excess 2-N ammonium hydroxide. The liberated base is extracted with methylene chloride and the extract evaporated to dryness. To the obtained residue, there is added a solution of 86.4 g. of ceric ammonium nitrate in 150 ml. of water and 150 ml. of glacial acetic acid. The mixture is stirred at 80° C. for 20 minutes, the color of the solution obtained changing from orange to light yellow. After cooling, 750 ml. of ice-water are added and the separated oil is extracted with methylene chloride. The organic phase is washed with 2-N ammonium hydroxide and a saturated sodium chloride solution, dried over sodium sulfate and concentrated to dryness. o-benzoyl-p-chlorophenylglyoxylic acid[ 2-(diethylamino)ethyl]methylamide is obtained as an oil which can be used in the process without further purification. With 2 mols of N-cyclohexylsulfamic acid, the base forms an addition compound which melts at 136°-138° C. (decomposition) after crystallization from isopropanol/diethyl ether.

Workup

  1. extractionThe liberated base is extracted with methylene chloride
  2. customthe extract evaporated to dryness
  3. additionTo the obtained residue, there is added a solution of 86.4 g
  4. customthe color of the solution obtained
  5. temperatureAfter cooling
  6. extractionthe separated oil is extracted with methylene chloride
  7. washThe organic phase is washed with 2-N ammonium hydroxide
  8. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d6a1f91c154f4c8c862449fe505798ea
Source dataset
uspto-grants-1978_10
Patent number
US04122265

Reaction notes

Loading…