Bromine → Ethyl 2-amino-alpha-methylbenzothiazole-6-acetate

HRID 660349Notes

Reaction equation

HRID 660349 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:15]([S-:17])#[N:16].[K+].BrBr>CC(O)=O>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[N:13]=[C:15]([NH2:16])[S:17][C:11]=2[CH:12]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 118009Ethyl 2-(4-aminophenyl)propanoateHCID 516872Potassium thiocyanate2×

Product 1

HCID 13477940Ethyl 2-amino-alpha-methylbenzothiazole-6-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent5×

Procedure

A mixture of 3 (3.13 g, 1 mmol) in CH3COOH (15 ml) was cooled to −5° in iced bath. A mixture KSCN (6.36 g, 4.04 mmol) in CH3COOH (15 ml) added to the flask that contained 4 and CH3COOH at −5° in iced bath. A solution of bromine (0.80 ml) in CH3COOH (10 ml) is added dropwise to a stirred mixture of 4, KSCN and CH3COOH at −5° in iced bath. The reaction mixture is stirred for 1 h at room temperature. The mixture is extracted with ethyl acetate. The extracts are washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (n-Hexane:EtOAc).

Workup

  1. temperaturewas cooled to −5° in iced bath
  2. customat −5°
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe extracts are washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (n-Hexane:EtOAc)

Sources & evidence

ORD record
ord-50a7f287a5f7480b913035996e63907b
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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