Acetic Acid → HCID 20228666, compound

HRID 1731367Notes

Reaction equation

HRID 1731367 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]4[S:18][C:17](=O)[NH:16][C:15]=4[C:20]=3C)[N:10]=[C:4]2[CH:3]=1.[CH2:22]=O.[CH3:24][NH:25][CH3:26].[C:27]([OH:30])(=O)C>CO>[CH3:24][N:25]([CH2:22][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]2=[N:10][C:9]=1[C:11]1[CH:12]=[CH:13][C:14]2[S:18][C:27](=[O:30])[N:16]([CH3:17])[C:15]=2[CH:20]=1)[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 131714942HCID 131714942, compound

Product 1

HCID 20228666HCID 20228666, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 5-(7-methylimidazo[1,2-a]pyridin-2-yl)-methyl-2-benzothiazolinone (1.9 g), 36% aqueous formaldehyde (1.07 g), 50% aqueous dimethylamine (1.16 g), acetic acid (772 mg) and methanol (10 ml) was stirred for 3 hours at 55°-60° C. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in a mixture of lN hydrochloric acid (10 ml), water (10 ml) and ethyl acetate (30 ml). The separated aqueous layer was adjusted to pH 7 with 20% aqueous solution of potassium carbonate and the resultant aqueous mixture was extracted with ethyl acetate (50 ml×2). The extract was dried over magnesium sulfate and evaporated under reduced pressure to give a crystalline residue, which was re-crystallized from ethyl acetate to afford pale brown needles of 5-(3-dimethylaminomethyl-7-methylimidazo[1,2-a]pyridin-2-yl)-3-methyl-2-benzothiazolinone (1.56 g). mp. 167°-168° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of lN hydrochloric acid (10 ml), water (10 ml) and ethyl acetate (30 ml)
  3. extractionthe resultant aqueous mixture was extracted with ethyl acetate (50 ml×2)
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto give a crystalline residue, which
  7. customwas re-crystallized from ethyl acetate

Sources & evidence

ORD record
ord-aa2e784b8226408dab75772365bb8ca5
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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