Hydrochloric Acid → 5-Benzyloxy-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one

HRID 367005Notes

Reaction equation

HRID 367005 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][C:8]([NH2:10])=[O:9])[S:5][CH:6]=1.[CH2:11]([O:18][C:19](=[CH:22]N(C)C)[CH:20]=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Cl>O.CN(C=O)C.CO>[CH2:11]([O:18][C:19]1[CH:22]=[C:7]([C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[C:8](=[O:9])[NH:10][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 7124452-(4-Methyl-1,3-thiazol-2-yl)acetamideHCID 545210022-Benzyloxy-3-(dimethylamino)acrolein

Product 1

HCID 1354930145-Benzyloxy-3-(4-methylthiazol-2-yl)-1H-pyridin-2-oneYield 73.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-Methylthiazol-2-yl)acetamide (0.016 mol), 2-benzyloxy-3-(N,N-dimethylamino)propenal (0.017 mol), sodium hydride (0.032 mol), methanol (1.3 ml) and DMF (100 ml) were heated at 70° C. for 4 h. The reaction was cooled, acidified with 5.0N HCl(aq), and poured into water. The resulting precipitate was collected by filtration and dried to give the product as a brown solid (11.7 mmol, 73%). δH (360 MHz; CDCl3) 9.38 (1H, s), 7.47-7.34 (7H, m), 7.09 (1H, s), 5.21 (2H, s), 2.69 (3H, s).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-240720d117dc422cba565788935b04ee
Source dataset
uspto-grants-2000_10
Patent number
US06133255

Reaction notes

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