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

HRID 652070Notes

Reaction equation

HRID 652070 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-9e76709d5f064993affb124e06813189
Source dataset
uspto-grants-1987_06
Patent number
US04670449

Reaction notes

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