2-Amino-4-chlorobenzenethiol → 5-chloro-2-(chloromethyl)-1,3-benzothiazole

HRID 2075550Notes

Reaction equation

HRID 2075550 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].[Cl:10][CH2:11][C:12](OCC)(OCC)OCC>C(O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[S:9][C:12]([CH2:11][Cl:10])=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 120002-Amino-4-chlorobenzenethiolHCID 3059222-Chloro-1,1,1-triethoxyethane

Product 1

HCID 107988395-chloro-2-(chloromethyl)-1,3-benzothiazoleYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

0.966 g of 2-amino-4-chloro-benzenethiol was dissolved in 10 ml of abs. ethanol. 1.44 g of 2-chloro-1,1,1-triethoxy-ethane were added and the reaction was heated at 60° C. overnight. The reaction mixture was then concentrated in vacuo, dissolved in diethyl ether and the organic phase was washed once each with 5% aqueous hydrochloric acid, followed by water and 10% aqueous sodium bicarbonate. The organic layer was dried with magnesium sulfate and concentrated in vacuo. Purification by flash chromatography on silica with heptanes/dichloromethane afforded 1.071 g of 5-chloro-2-chloromethyl benzothiazole as a yellow solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutiondissolved in diethyl ether
  3. washthe organic phase was washed once each with 5% aqueous hydrochloric acid
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica with heptanes/dichloromethane

Sources & evidence

ORD record
ord-ee039c04170c4345ae3926a604cb7d8a
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

Loading…