Sodium Hydroxide → 3-Propyl-2lambda~6~-pyrido[2,3-c][1,2,6]thiadiazine-2,2,4(1H,3H)-trione

HRID 66037Notes

Reaction equation

HRID 66037 reaction equation
[CH2:1]([NH:4][S:5]([NH:8][C:9]1[C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=[CH:11][N:10]=1)(=[O:7])=[O:6])[CH2:2][CH3:3].[OH-].[Na+]>O>[CH2:1]([N:4]1[S:5](=[O:7])(=[O:6])[NH:8][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:15]1=[O:17])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22756776HCID 22756776, compound

Product 1

HCID 227567853-Propyl-2lambda~6~-pyrido[2,3-c][1,2,6]thiadiazine-2,2,4(1H,3H)-trione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-(((n-propylamino)sulfonyl)amino)-3-pyridinecarboxylate (15.7 grams; 0.057 mole), 95 ml of water and 10.5 ml of 50 percent aqueous sodium hydroxide were mixed and the resulting reaction mixture stirred for about 11/4 hours at ambient temperatures. The reaction mixture was extracted with two -- 50 ml portions of methylene chloride and one -- 50 ml portion of ether to remove impurities. The aqueous layer was separated from the organic layer and acidified to a pH of about 4.5 with concentrated hydrochloric acid. The solution was filtered and the filtrate acidified to a pH of about 1. The resulting product precipitate was recovered by filtration, dissolved in acetone and the solution filtered and dried with magnesium sulfate. The mixture was again filtered and the filtrate reduced in vacuo to obtain the title compound as a yellow powder having a melting point of 208° C.-210° C.

Workup

  1. customthe resulting reaction mixture
  2. extractionThe reaction mixture was extracted with two
  3. custom50 ml portions of methylene chloride and one -- 50 ml portion of ether to remove impurities
  4. customThe aqueous layer was separated from the organic layer
  5. filtrationThe solution was filtered
  6. filtrationThe resulting product precipitate was recovered by filtration
  7. dissolutiondissolved in acetone
  8. filtrationthe solution filtered
  9. dry with materialdried with magnesium sulfate
  10. filtrationThe mixture was again filtered

Sources & evidence

ORD record
ord-3ceb2a91f6e8402fa68fe14141157bcd
Source dataset
uspto-grants-1978_12
Patent number
US04129734

Reaction notes

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