Bromine → HCID 12894509, compound

HRID 660343Notes

Reaction equation

HRID 660343 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:13]([S-:15])#[N:14].[K+].BrBr>CC(O)=O>[NH2:14][C:13]1[S:15][C:7]2[CH:6]=[C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:4]=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 430264-Aminohydratropic acidHCID 516872Potassium thiocyanate2×

Product 1

HCID 12894509HCID 12894509, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent5×

Procedure

A mixture of 2 (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-37ca9cf27b464f2a80c6b13b3a2a4ae1
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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