Acetone → HCID 21200530, compound

HRID 1739111Notes

Reaction equation

HRID 1739111 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].C([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])C.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C[C:24](C)=[O:25]>C(Cl)Cl>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[CH3:1][N:2]([CH3:4])[NH:3][C:24]([C:22]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:8][NH:7][CH2:10][CH2:11]1)=[O:25]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 59761,1-DimethylhydrazineHCID 6101p-Toluenesulfonic acidHCID 8471Triethylamine

Product 1

HCID 21200530HCID 21200530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 7.15 g of the compound obtained in step B of PREPARATION 1.28 in 60 ml of DCM is cooled to 5° C., a solution of 1.44 g of 1,1-dimethylhydrazine and 4.04 g of triethylamine in 20 ml of DCM is added dropwise and the reaction mixture is left stirring overnight at RT. It is concentrated under vacuum, the residue is taken up with water, the product is extracted with AcOEt, the organic phase is washed with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The product obtained is dissolved in 100 ml of acetone, a solution of 3.59 g of p-toluenesulphonic acid in 10 ml of acetone is added rapidly and the mixture is concentrated under vacuum. The residue is taken up in an ether/DCM mixture and the precipitate formed is drained. 9.65 g of the expected product are obtained.

Workup

  1. waitthe reaction mixture is left
  2. concentrationIt is concentrated under vacuum
  3. extractionthe product is extracted with AcOEt
  4. washthe organic phase is washed with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe product obtained
  8. concentrationthe mixture is concentrated under vacuum
  9. customthe precipitate formed

Sources & evidence

ORD record
ord-7c64245ad5b447dc8fab9b328e635b53
Source dataset
uspto-grants-1999_10
Patent number
US05965580

Reaction notes

Loading…