Ethanol → HCID 23047249, compound

HRID 2107041Notes

Reaction equation

HRID 2107041 reaction equation
[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2([CH3:20])[CH3:19].[Na].C(O)C.[N+:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]>O>[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:32](=[O:33])[C:31]1[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:36][CH:35]=1)[C:13](=[O:18])[C:12]2([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 85024-Nitrobenzoyl chlorideHCID 5360545SodiumHCID 15111517HCID 15111517, compound

Product 1

HCID 23047249HCID 23047249, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.9 g (10 mmol) 1,3-dihydro-5(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4 thiadiazin-5-yl)-3,3 dimethyl-2H-indol-2-one (Example 3), 0.4 g (10 mmol) sodium hydroxyde and 100 ml ethanol were refluxed 30mn. After evaporation of the solvent, the residue was dissolved in 50 ml DMF and 1.86 g (10 mmol) p-nitrobenzoyl chloride were added while keeping the temperature under 30° C. The mixture was stirred 2 hrs at room temperature, diluted with 100 ml water, extracted with ethyl acetate. The organic layers were washed with brine and dried over magnesium sulfate. The residue was purified by column chfomatography on silica (eluent:ethylacetate/hexane:1/1) and the major fraction was triturated in isopropyl ether and dried under vacuum.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in 50 ml DMF
  3. customunder 30° C
  4. extractionextracted with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe residue was purified by column chfomatography on silica (eluent:ethylacetate/hexane:1/1)
  8. customthe major fraction was triturated in isopropyl ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-b4802c41bde24d2f86f7d5c1ab56361f
Source dataset
uspto-grants-1990_06
Patent number
US04933336

Reaction notes

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