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

HRID 660345Notes

Reaction equation

HRID 660345 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.

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

Sources & evidence

ORD record
ord-09670237ff58432f87c95ca51c860f9a
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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