Ammonium thiocyanate → HCID 10422503, compound

HRID 728131Notes

Reaction equation

HRID 728131 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.[S-:16][C:17]#[N:18].[NH4+].BrBr>C(O)(=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:17]([NH2:18])[S:16][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 24408BromineHCID 2332894-[2-(Pyridin-2-yl)ethyl]aniline

Product 1

HCID 10422503HCID 10422503, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 2-[2-(4-aminophenyl)ethyl]pyridine (5.94 g) and ammonium thiocyanate (4.56 g) in acetic acid (50 ml) was stirred at ambient temperature for one hour. A solution of bromine (4.8 g) in acetic acid (5 ml) was dropwise added to the above mixture at 18° to 23° C. under stirring and the resultant mixture was stirred at ambient temperature for 3 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The solution was acidified to pH 1.0 with hydrochloric acid. The separated aqueous layer was adjusted to pH 7.5 with aqueous 20% potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from ethyl acetate to give 6-[2-(2-pyridyl)ethyl]-2-aminobenzothiazole (4.8 g).

Workup

  1. stirringunder stirring
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  4. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9da9c3e93dec4c26820c40403382161c
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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