Acetic Acid → HCID 15027628, compound

HRID 1090644Notes

Reaction equation

HRID 1090644 reaction equation
[N+:1]([C:4]1[C:5](=[O:18])[N:6]([CH2:15][CH2:16][CH3:17])[C:7](=[O:14])[N:8]2[CH2:13][CH2:12][CH2:11][S:10][C:9]=12)([O-])=O.[C:19](O)(=[O:21])[CH3:20]>[Zn]>[C:19]([NH:1][C:4]1[C:5](=[O:18])[N:6]([CH2:15][CH2:16][CH3:17])[C:7](=[O:14])[N:8]2[CH2:13][CH2:12][CH2:11][S:10][C:9]=12)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15027575HCID 15027575, compound

Product 1

HCID 15027628HCID 15027628, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Zinc powder (1,21 g) was added to a solution of 9-nitro-7-propyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (1 g) in acetic acid (10 ml) and the mixture was refluxed for 4 hours. An insoluble material was removed by filtration, and the filtrate was concentrated to obtain syrup. The syrup was purified by column chromatography on silica gel. The resulting crude crystals were recrystallized from methylene chloride-hexane to give colorless needles (0.83 g, 79%).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customAn insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customto obtain syrup
  5. customThe syrup was purified by column chromatography on silica gel
  6. customThe resulting crude crystals were recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-4ec28d5cb51149edac51517f914a5ac3
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

Loading…