N-Methylbenzylamine → 3-Methyl-6-[2-(N-methyl-N-benzylamino)ethyl]benzothiazolinone

HRID 326243Notes

Reaction equation

HRID 326243 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][N:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH2:20][CH2:21]Br)=[CH:19][C:14]=2[S:13](=[O:23])[CH2:12]1>O1CCOCC1>[CH3:10][N:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH2:20][CH2:21][N:2]([CH3:1])[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:19][C:14]=2[S:13](=[O:23])[CH2:12]1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 701838363-Methyl-6-(2-bromoethyl)benzothiazolinone

Product 1

HCID 678520773-Methyl-6-[2-(N-methyl-N-benzylamino)ethyl]benzothiazolinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.04 mol of N-methyl-N-benzylamine and 0.02 mol of 3-methyl-6-(2-bromoethyl)benzothiazolinone, the latter being dissolved beforehand in 120 cm3 of dioxane, are introduced into a 100-cm3 ground-necked flask fitted with a reflux condenser. The mixture is heated to reflux for 96 hours with magnetic stirring. After cooling, the reaction mixture is filtered and the filtrate is then evaporated on a water bath under vacuum. The residue is taken up with 50 cm3 and alkalinized with 10 cm3 of normal sodium hydroxide solution.

Workup

  1. additionare introduced into a 100-cm3 ground-necked flask
  2. customfitted with a reflux condenser
  3. temperatureThe mixture is heated
  4. temperatureto reflux for 96 hours with magnetic stirring
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture is filtered
  7. customthe filtrate is then evaporated on a water bath under vacuum

Sources & evidence

ORD record
ord-f335f6f1064946e6b7a6b84b7aedfdf0
Source dataset
uspto-grants-1993_12
Patent number
US05268381

Reaction notes

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