Benzocaine → Ethyl 2-Aminobenzothiazole-6-carboxylate

HRID 1498955Notes

Reaction equation

HRID 1498955 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 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 4-aminobenzoate (23.2 g, 140.4 mmol) and potassium thiocyanate (40.9 g, 420.9 mmol) were dissolved in acetic acid (280 ml), and under an ice cooling, bromine (22.4 g, 140.4 mmol) was slowly added thereto. The mixture was stirred under an ice cooling for 10 minutes and then stirred at a room temperature overnight. To the mixture, purified water was added and then ice was added. Thereafter, the resulting mixture was neutralized with ammonia water. The precipitate was separated by filtration, washed with purified water, and then subjected to through circulation drying to give the title compound (25.2 g, 81%) as a white powder.

Workup

  1. stirringstirred at a room temperature overnight
  2. customTo the mixture, purified water
  3. additionwas added
  4. additionice was added
  5. customThe precipitate was separated by filtration
  6. washwashed with purified water
  7. customdrying

Sources & evidence

ORD record
ord-d1c6956786ec4dfc80f6715af7c4bd16
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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