3,4-Dimethoxy-1,2,5-thiadiazole 1-oxide → HCID 20199216, compound

HRID 543138Notes

Reaction equation

HRID 543138 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:7][C:8]([CH3:29])=[C:9]([C:25]([O:27][CH3:28])=[O:26])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[Cl:24])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH3:30][O:31][C:32]1[C:36](OC)=[N:35][S:34](=[O:39])[N:33]=1>CO>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH:10]1[C:9]([C:25]([O:27][CH3:28])=[O:26])=[C:8]([CH3:29])[NH:7][C:6]([CH2:5][O:4][CH2:3][CH2:2][NH:1][C:36]2[C:32]([O:31][CH3:30])=[N:33][S:34](=[O:39])[N:35]=2)=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 13663190HCID 13663190, compound

Product 1

HCID 20199216HCID 20199216, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-Aminoethoxymethyl]-3-ethoxycarbonyl-4-(2,3-dichlorophenyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (0.5 g) and 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (0.2 g) were dissolved in methanol (15 ml) and heated at reflux for 14 hours. The solvent was evaporated and the residue chromatographed on silica "Kieselgel 60H" (Trade Mark), eluting with ethyl acetate. The product-containing fractions were combined and evaporated to give an oil which was triturated in ethyl acetate to give the title compound as a solid, yield 0.14 g, m.p. 183°-185°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 14 hours
  3. customThe solvent was evaporated
  4. customthe residue chromatographed on silica "Kieselgel 60H" (Trade Mark)
  5. washeluting with ethyl acetate
  6. customevaporated
  7. customto give an oil which
  8. customwas triturated in ethyl acetate

Sources & evidence

ORD record
ord-ad830e5e7fe8473da36774480af08cc3
Source dataset
uspto-grants-1987_04
Patent number
US04661485

Reaction notes

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