Potassium Carbonate → HCID 10083053, compound

HRID 728132Notes

Reaction equation

HRID 728132 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[S-:15][C:16]#[N:17].[NH4+].BrBr.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O.C(OCC)(=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][C:5]1[CH:13]=[CH:14][C:2]2[N:1]=[C:16]([NH2:17])[S:15][C:3]=2[CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 4595252-(4-Aminobenzyl)pyridine

Product 1

HCID 10083053HCID 10083053, compoundYield 14.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-aminobenzyl)pyridine (4.5 g) and ammonium thiocyanate (3.7 g) in acetic acid (50 ml) was stirred at ambient temperature for 1 hour. A solution of bromine (1.3 ml) in acetic acid (5 ml) was dropwise added thereto at 10° to 15° C. under stirring and the resulting mixture was stirred at 10° to 20° C. for 1 hour. A mixture of ethyl acetate and water was added to the reaction mixture and the mixture was adjusted to pH 7.5 with potassium carbonate. An insoluble material was filtered off and the filtrate was separated. The resulting organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated and triturated with ethyl acetate. The precipitate was collected by filtration and dried to give 6-[(2-pyridyl)methyl]-2-aminobenzothiazole (0.83 g).

Workup

  1. stirringthe resulting mixture was stirred at 10° to 20° C. for 1 hour
  2. additionwas added to the reaction mixture
  3. filtrationAn insoluble material was filtered off
  4. customthe filtrate was separated
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customtriturated with ethyl acetate
  9. filtrationThe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-e0167ebf1aa54bb4804638296c761734
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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