Potassium Carbonate → HCID 9972556, compound

HRID 728133Notes

Reaction equation

HRID 728133 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]3[CH:19]=2)=[CH:4][CH:3]=1.[S-:20][C:21]#[N:22].[NH4+].BrBr.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O.C(OCC)(=O)C>[CH3:18][C:16]1[CH:15]=[CH:14][N:13]2[CH:19]=[C:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[C:21]([NH2:22])[S:20][C:3]=4[CH:4]=3)[N:11]=[C:12]2[CH:17]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 10083527HCID 10083527, compound

Product 1

HCID 9972556HCID 9972556, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[2-(4-aminophenyl)ethyl]-7-methylimidazo[1,2-a]pyridine (2.5 g) and ammonium thiocyanate (1.5 g) in acetic acid (25 ml) was stirred at ambient temperature for 1 hour. A solution of bromine (0.6 ml) in acetic acid (3 ml) was dropwise added thereto at 15° to 18° 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. The separated organic layer was washed with brine and dried over magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (19:1 V/V). The eluted fractions containing desired product were evaporated to give 6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-aminobenzothiazole (0.43 g).

Workup

  1. stirringthe resulting mixture was stirred at 10° to 20° C. for 1 hour
  2. additionwas added to the reaction mixture
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product obtained by concentration
  6. customwas purified by silica gel column chromatography
  7. washeluting with a mixture of chloroform and methanol (19:1 V/V)
  8. additionThe eluted fractions containing desired product
  9. customwere evaporated

Sources & evidence

ORD record
ord-5be07352805b4300930c3ca073f50a4e
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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