Isopropylamine → HCID 178456812, compound

HRID 1066172Notes

Reaction equation

HRID 1066172 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7](OCC)[N:8]([CH3:12])[S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[CH:18]([NH2:21])([CH3:20])[CH3:19].[O-]CC.[Na+].[Na]>C(O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:21][CH:18]([CH3:20])[CH3:19])[N:8]([CH3:12])[S:9](=[O:10])(=[O:11])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21197906HCID 21197906, compound

Product 1

HCID 178456812HCID 178456812, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of crude 7-chloro-3-ethoxy-2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide (0.45 g) and isopropylamine (4 ml) in an ethanolic sodium ethoxide solution, prepared by dissolving 0.4 g of sodium in 10 ml of ethanol, was refluxed for 3 hours and then neutralized with 4M acetic acid. The mixture was evaporated to dryness and partitioned between 25 ml of water and 25 ml of dichloromethane. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column with a 7:3 mixture of n-heptane and ethyl acetate as solvent to give the title compound;

Workup

  1. customprepared
  2. temperaturewas refluxed for 3 hours
  3. customThe mixture was evaporated to dryness
  4. custompartitioned between 25 ml of water and 25 ml of dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by chromatography on a silica gel column with a 7:3 mixture of n-heptane and ethyl acetate as solvent

Sources & evidence

ORD record
ord-bc844a6035704a35b793ae1369157936
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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