2-Methoxyethanol → HCID 19075428, compound

HRID 1600236Notes

Reaction equation

HRID 1600236 reaction equation
[Na].[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].Cl[C:9]1[C:13]([C:14]2[CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][CH:19]=2)=[N:12][S:11][N:10]=1.[CH3:21][O:22][CH2:23][CH2:24][OH:25]>>[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[CH3:21][O:22][CH2:23][CH2:24][O:25][C:9]1[C:13]([C:14]2[CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][CH:19]=2)=[N:12][S:11][N:10]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 19075340HCID 19075340, compound

Product 1

HCID 19075428HCID 19075428, compound

Conditions

Temperature
50 °C

Procedure

To a solution of sodium (120 mg, 5 mmol) in 2-methoxyethanol (10 ml) was added 3-(3-chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine oxalate (310 mg, 1 mmol). The mixture was stirred at 50° C. for 18 h and evaporated. The residue was dissolved in water and extracted with ethyl acetate. The combined organic phases were dried and evaporated. The title compound was crystallized as the oxalate salt from acetone to yield 270 mg. (M.p. 152.1° C.; M+ : 253; Compound 15).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customevaporated
  6. customThe title compound was crystallized as the oxalate salt from acetone
  7. customto yield 270 mg

Sources & evidence

ORD record
ord-151bfdab6fc14faea985ab078b660868
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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