Water → HCID 53775860, compound

HRID 581053Notes

Reaction equation

HRID 581053 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:4][CH:3]=1.C1(=O)O[CH2:22][CH2:21][O:20]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][CH2:22][CH2:21][OH:20])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 53950369HCID 53950369, compound

Product 1

HCID 53775860HCID 53775860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1.05 g (3.8 mmol) of 2-(4-chlorobenzyl)-6-hydroxy-benzothiazole and 0.67 g (7.6 mmol) of ethylene carbonate are dissolved in 20 ml of dimethylformamide and after the addition of 2.1 g (15.2 mmol) of potassium carbonate the mixture is stirred for 2 hours at 120° C. It is then added to water and extracted with ethyl acetate. After the extracts have been evaporated down the residue is purified by column chromatography on silica gel (eluant: ethyl acetate). Yield: 1.6 g (69% of theory).

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter the extracts have been evaporated down the residue
  3. customis purified by column chromatography on silica gel (eluant: ethyl acetate)

Sources & evidence

ORD record
ord-6664e5cbe96b4170b342e2950119de55
Source dataset
uspto-grants-1999_07
Patent number
US05919807

Reaction notes

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