Sulfuric Acid → 1,2-Dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarboxamide

HRID 1982211Notes

Reaction equation

HRID 1982211 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[NH:12][C:11](=[O:13])[C:10]([C:14]#[N:15])=[CH:9][C:8]=1[C:16]1[N:17]=[C:18]([CH3:21])[S:19][CH:20]=1.[OH-:22].[NH4+]>>[CH3:6][C:7]1[NH:12][C:11](=[O:13])[C:10]([C:14]([NH2:15])=[O:22])=[CH:9][C:8]=1[C:16]1[N:17]=[C:18]([CH3:21])[S:19][CH:20]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 28012566-Methyl-5-(2-methyl-1,3-thiazol-4-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 155921671,2-Dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarboxamide

Procedure

To an ice cold stirred 150 ml portion of concentrated sulfuric acid was added over a 5 minute period 64.2 g of finely powdered 1,2-dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarbonitrile and the resulting mixture was stirred in an ice bath for 30 minutes and then allowed to stand at room temperature overnight. The reaction mixture was poured onto ice (800 ml beaker half filled) and then neutralized by adding aqueous ammonium hydroxide solution. The tan solid that separated was collected, washed with water, recrystallized from dimethylformamide and dried in an oven at 90° C. for 2 days to produce 59.2 g of 1,2-dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarboxamide, m.p. >300° C. with decomposition.

Workup

  1. waitto stand at room temperature overnight
  2. additionThe reaction mixture was poured onto ice (800 ml beaker half filled)
  3. customThe tan solid that separated was collected
  4. washwashed with water
  5. customrecrystallized from dimethylformamide
  6. customdried in an oven at 90° C. for 2 days

Sources & evidence

ORD record
ord-36c60b804c9f4bda816236534f13b7c4
Source dataset
uspto-grants-1986_06
Patent number
US04595762

Reaction notes

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