Water → HCID 13674821, compound

HRID 1649985Notes

Reaction equation

HRID 1649985 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].CS(O[CH:21]([CH3:34])[CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])(=O)=O.O>C1(C)C=CC=CC=1>[C:24]1(=[O:33])[N:23]([CH2:22][CH:21]([N:11]([C:5]2[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=2[CH3:3])[S:12]([CH3:15])(=[O:14])=[O:13])[CH3:34])[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 686475HCID 686475, compoundHCID 14713891HCID 14713891, compound

Product 1

HCID 13674821HCID 13674821, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.15 g of a 80% mineral oil dispersion of sodium hydride are added in some portions to a solution of 1.0 g (5 mmoles) of N-(2,6-dimethylphenyl)-methanesulfonamide in 20 ml of dry toluene, and the mixture is heated to 100°-105° C. within one hour. A solution of 1.4 g (5 mmoles) of N-(β-methanesulfonyloxy-propyl)-phthalimide in 15 ml of toluene is added dropwise to the mixture within 0.5 hours at the same temperature, and the mixture is stirred then at 100°-105° C. for 10 hours. The mixture is cooled, 20 ml of water are added dropwise to it, thereafter the toluene phase is separated, washed twice with 10 ml of 1 n aqueous sodium hydroxide solution and thrice with 20 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The solid residue is triturated with dry diethyl ether. 0.46 g (23.8%) of crude 1-phthalimido-2-[N-(2,6-dimethylphenyl)-methanesulfonamido]-propane are obtained. The crude product is stirred at room temperature in 100 ml of diethyl ether for one hour to obtain a purified product melting at 196°-198° C.

Workup

  1. temperaturethe mixture is heated to 100°-105° C. within one hour
  2. temperatureThe mixture is cooled
  3. customthe toluene phase is separated
  4. washwashed twice with 10 ml of 1 n aqueous sodium hydroxide solution and thrice with 20 ml of water
  5. dry with materialeach, dried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe solid residue is triturated with dry diethyl ether

Sources & evidence

ORD record
ord-5269cb56e6d14c5bb2bb17ad77f66b95
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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