Water → HCID 54182031, compound

HRID 581054Notes

Reaction equation

HRID 581054 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([S:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][O:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([S:9][C:10]3[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 53814322HCID 53814322, compound

Product 1

HCID 54182031HCID 54182031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.74 g (2.5 mmol) of 6-hydroxy-2-(4-chlorophenylmercapto)-benzothiazole are dissolved in 20 ml of dimethylformamide and after the addition of 2.16 g (10 mmol) of 1.4-dibromobutane and 2.07 g (15 mmol) of potassium carbonate the resulting mixture is stirred for 20 hours at ambient temperature. The mixture is then added to water and extracted with ethyl acetate. The extracts are dried and evaporated down. The evaporation residue is purified by column chromatography on silica gel (eluant: petroleum ether/ethyl acetate=4:1). Yield: 0.85 g (79.3% of theory), oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extracts are dried
  3. customevaporated down
  4. customThe evaporation residue is purified by column chromatography on silica gel (eluant: petroleum ether/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c30289873e64418b94266c63d10f8eb5
Source dataset
uspto-grants-1999_07
Patent number
US05919807

Reaction notes

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