Benzocaine → Ethyl 2-Aminobenzothiazole-6-carboxylate

HRID 1883210Notes

Reaction equation

HRID 1883210 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[S-:13][C:14]#[N:15].[K+].BrBr>C(O)(=O)C>[NH2:15][C:14]1[S:13][C:12]2[CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 601008Ethyl 2-Aminobenzothiazole-6-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl p-aminobenzoate (23.2 g) and potassium thiocyanate (40.9 g) in acetic acid (280 mL) was cooled to 0° C., and thereto was added dropwise bromine (22.4 g), and the mixture was stirred at 0° C. for 20 minuts, and stirred at room temperature for 135 minutes, and stirred for 5 hours. The precipitated solid was collected by filtration to give ethyl 2-amino-1,3-benzothiazole-6-carboxylate (9.62 g, 31%)

Workup

  1. stirringstirred at room temperature for 135 minutes
  2. stirringstirred for 5 hours
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-171f44b86dd648258f2f7b256cb338d2
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

Loading…