Potassium Carbonate → HCID 15718359, compound

HRID 1199694Notes

Reaction equation

HRID 1199694 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[OH:12][CH2:13][C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][O:12][CH2:13][C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12078alpha-Chloro-m-nitrotolueneHCID 268122(1,3-Benzothiazol-2-yl)methanol

Product 1

HCID 15718359HCID 15718359, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.60 g of 3-nitrobenzyl chloride, 1.3 g of 2-hydroxymethylbenzothiazole and 0.54 of potassium carbonate in 20 ml of acetone was stirred at room temperature for 1.5 hours and then refluxed for 30 minutes. After evaporation of acetone under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and dried over magnesium sulfate, followed by evaporation of the solvent under reduced pressure. The residue was purified through a silica gel column chromatography by use of ethyl ether-n-hexane to obtain 1.7 g (yield 73%) of the title compound.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customAfter evaporation of acetone under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customfollowed by evaporation of the solvent under reduced pressure
  7. customThe residue was purified through a silica gel column chromatography by use of ethyl ether-n-hexane

Sources & evidence

ORD record
ord-d0bfd630b5aa4fe991245cafe6b1430b
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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