HCID 13335781, compound → HCID 13335791, compound

HRID 637753Notes

Reaction equation

HRID 637753 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH:5]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH2:21][CH2:22][Cl:23])(=[O:3])[CH3:2]>C(O)C.C(NCC)C>[ClH:23].[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH:5]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH2:21][CH2:22][N:4]([CH2:5][CH3:13])[CH2:1][CH3:2])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13335781HCID 13335781, compound

Product 1

HCID 13335791HCID 13335791, compoundYield 161.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8021DiethylamineSolvent

Procedure

To the solution of 3.48 g of 3-acetyl-2-[2-(3-chloropropoxy)phenyl]benzothiazoline in 20 ml of ethanol, 10.3 ml of diethylamine is added and the mixture is refluxed for 2 hours. After removal of ethanol and excess amount of diethylamine in vacuo, ethyl acetate and water are added to the residue. The organic layer is extracted with N-hydrochloric acid, the acidic layer is alkalinized with N-sodium hydroxide solution and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is removed off in vacuo and the resulting oil is dissolved in methanol. To the solution hydrochloric acid in ethyl acetate is added to give 3.4 g (80%) of the titled compound.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customAfter removal of ethanol and excess amount of diethylamine in vacuo, ethyl acetate and water
  3. additionare added to the residue
  4. extractionThe organic layer is extracted with N-hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent is removed off in vacuo
  9. dissolutionthe resulting oil is dissolved in methanol
  10. additionTo the solution hydrochloric acid in ethyl acetate is added

Sources & evidence

ORD record
ord-7a381b587acb4032b743272b2b5ff1af
Source dataset
uspto-grants-1985_12
Patent number
US04558125

Reaction notes

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