2-Amino-4-methylpyridine → HCID 20228729, compound

HRID 1731330Notes

Reaction equation

HRID 1731330 reaction equation
Br[CH:2]([CH3:16])[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](=[O:13])[N:10]([CH3:14])[C:9]=2[CH:15]=1)=O.[NH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1>C(#N)C>[CH3:16][C:2]1[N:19]2[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:18]2=[N:17][C:3]=1[C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](=[O:13])[N:10]([CH3:14])[C:9]=2[CH:15]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 139361575-(2-Bromopropanoyl)-3-methyl-1,3-benzothiazol-2(3H)-one

Product 1

HCID 20228729HCID 20228729, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(2-bromopropionyl)-3-methyl-2-benzothiazolinone (3.0 g) and 2-amino-4-methylpyridine (3.24 g) in acetonitrile (100 ml) was refluxed for 8 hours. The reaction mixture was concentrated to about a half volume and poured into a mixture of water and ethyl acetate. The resulitng mixture was acidified to PHO.5 with 10% hydrochloric acid. The precipitate was collected by filtration and washed successively with water and ethyl acetate. The resulting precipitate was added to a mixture of ethyl acetate, tetrahydrofuran and water, and the mixture was adjust to pH 7.0 with 20% aqueous potassium carbonate solution. The separated organic alyer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to afford a crystalline residue. The residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 5-(3,7-dimethylimidazo-[1,2-a]pyridin-2-yl)-3-methyl-2-benzothiazolinone (1.96 g).

Workup

  1. concentrationThe reaction mixture was concentrated to about a half volume
  2. additionpoured into a mixture of water and ethyl acetate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed successively with water and ethyl acetate
  5. additionThe resulting precipitate was added to a mixture of ethyl acetate, tetrahydrofuran and water
  6. washThe separated organic alyer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto afford a crystalline residue
  10. customThe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-69bad708e9a041949dff2a9603529942
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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