2-Amino-3-methylpyridine → HCID 20228680, compound

HRID 1731328Notes

Reaction equation

HRID 1731328 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](=[O:13])[NH:10][C:9]=2[CH:14]=1)=O.[CH3:15][C:16]1[C:17]([NH2:22])=[N:18][CH:19]=[CH:20][CH:21]=1>C(#N)C>[CH3:15][C:16]1[C:17]2[N:18]([CH:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]4[S:12][C:11](=[O:13])[NH:10][C:9]=4[CH:14]=3)[N:22]=2)[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 15054199HCID 15054199, compound

Product 1

HCID 20228680HCID 20228680, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-bromoacetyl 2-benzothiazolinone (1.75g) and 3-methyl-2-aminopyridine [2.07 g] in acetonitrile [100 ml] was refluxed for 4 hours and the reaction mixture was evaporated in vacuo. To the residue was added a mixture of water, ethyl acetate and tetrahydrofuran. The resulting mixture was adJusted to pH 8.0 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to afford a crystalline residue, which was recrystallized from a mixture of tetrahydrofuran and diethyl ether to give 5-(8-methylimidazo-[1,2-a]pyridin-2-yl)-2-benzothiazolinone (1.18 g). mp. 272° C. (dec.).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added
  3. additiona mixture of water, ethyl acetate and tetrahydrofuran
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto afford a crystalline residue, which
  8. customwas recrystallized from a mixture of tetrahydrofuran and diethyl ether

Sources & evidence

ORD record
ord-1634ad9bdf9143cf92e851d8c03e2bb0
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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