Hydrochloric Acid → HCID 19913604, compound

HRID 1090648Notes

Reaction equation

HRID 1090648 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[CH:12]=[C:7]2[S:8][CH2:9][CH2:10][CH2:11][N:6]2[C:5]1=[O:15])[CH2:2][CH3:3].[CH2:16]=O.[ClH:18].[CH3:19][NH:20][CH3:21].Cl>C(O)(=O)C>[Cl-:18].[CH3:19][NH+:20]([CH2:16][C:12]1[C:13](=[O:14])[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:15])[N:6]2[CH2:11][CH2:10][CH2:9][S:8][C:7]=12)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 15027560HCID 15027560, compound

Product 1

HCID 19913604HCID 19913604, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7-propyl-3,4-dihydro-2H,5H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (1 g), paraformaldehyde (0.22 g) and dimethylamine hydrochloride (0.51 g) in acetic acid (25 ml) was refluxed for 18 hours. The reaction solution was concentrated dryness, and the resulting residue was dissolved in water. Then, the solution was made basic with 1N aquaous sodium hydroxide, followed by extraction of the product with methylene chloride. After washing with water and drying, the organic layer was concentrated to dryness to obtain a syrup. The syrup was converted to the hydrochloride to form crystals, which were recrystallized from ethanol-ethyl acetate to give colorless prisms (0.46 g, 33%).

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationThe reaction solution was concentrated dryness
  3. dissolutionthe resulting residue was dissolved in water
  4. extractionfollowed by extraction of the product with methylene chloride
  5. washAfter washing with water
  6. customdrying
  7. concentrationthe organic layer was concentrated to dryness
  8. customto obtain a syrup
  9. customto form crystals, which
  10. customwere recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-1f64d4a8bcfd45d39bb9bffcf86d2422
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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