Chloroacetyl chloride → 2-(Chloromethyl)benzothiazole

HRID 1725598Notes

Reaction equation

HRID 1725598 reaction equation
[Cl:1][CH2:2][C:3](Cl)=O.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[SH:13]>CN(C)C=O.ClCCl>[Cl:1][CH2:2][C:3]1[S:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=1

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 87132-Aminothiophenol

Product 1

HCID 3049782-(Chloromethyl)benzothiazoleYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (81.6 ml) is added dropwise to a solution composed of 2-aminothiophenol (112 ml, 1.04 mol), dichloromethane (1.2 l) and three drops of dimethylformamide, while the temperature is kept below 40° C. After stirring for 18 hours, the precipitate formed is filtered off by suction and then dissolved in a minimum amount of water. This aqueous phase is extracted with pentane and the extracts are concentrated under vacuum at room temperature, giving 120 g (65%) of a flaky solid.

Workup

  1. customis kept below 40° C
  2. customthe precipitate formed
  3. filtrationis filtered off by suction
  4. dissolutiondissolved in a minimum amount of water
  5. extractionThis aqueous phase is extracted with pentane
  6. concentrationthe extracts are concentrated under vacuum at room temperature

Sources & evidence

ORD record
ord-ad18f4541d5f435983ecafee418d7d7d
Source dataset
uspto-grants-2009_02
Patent number
US07491733B2

Reaction notes

Loading…