Ethanol → HCID 19831183, compound

HRID 1493310Notes

Reaction equation

HRID 1493310 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]([CH3:26])=[C:6]([N+:23]([O-:25])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl.[NH2:28][CH2:29][CH2:30][SH:31].[OH-:32].[Na+].[CH3:34][CH2:35][OH:36]>>[C:9]([OH:11])(=[O:10])/[CH:8]=[CH:34]/[C:35]([OH:32])=[O:36].[NH2:28][CH2:29][CH2:30][S:31][CH2:2][C:3]1[NH:4][C:5]([CH3:26])=[C:6]([N+:23]([O-:25])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 17976877HCID 17976877, compound

Product 1

HCID 19831183HCID 19831183, compound

Procedure

A solution of 2-chloromethyl-3-carboethoxy-4-(m-nitrophenyl)-5-nitro-6-methyl-1,4-dihydropyridine (1.5 g) in EtOH (15 ml) is added dropwise at 0° C. under N2 atmosphere to a solution of cysteamine hydrochloride (0.9 g) and sodium hydroxide (0.32 g) in EtOH (45 ml). After two hours the solution is acidified (pH ≃ 4) with AcOH, evaporated under reduced pressure and the residue is dissolved in water (50 ml) and extracted with Et2O (2×20 ml). The ethereal extractions are discarded, the water layer is made basic with NaHCO3 and extracted with AcOEt (2×20 ml); the organic phase is washed with water (3×10 ml), dried (Na2SO4), added to a solution of fumaric acid (0.45 g) in MeOH (15 ml), and evaporated to dryness. The residue is crystallized from AcOEt to give 1.9 g of 2-[(2-aminoethyl)thio]methyl-3-carboethoxy-4-(m-nitrophenyl)-5-nitro-6-methyl-1,4-dihydropyridine fumarate (C18H22N4O6S.C4H4O4), m.p. 182°-185° C.

Workup

  1. custom(pH ≃ 4) with AcOH, evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in water (50 ml)
  3. extractionextracted with Et2O (2×20 ml)
  4. extractionThe ethereal extractions
  5. extractionextracted with AcOEt (2×20 ml)
  6. washthe organic phase is washed with water (3×10 ml)
  7. dry with materialdried (Na2SO4)
  8. additionadded to a solution of fumaric acid (0.45 g) in MeOH (15 ml)
  9. customevaporated to dryness
  10. customThe residue is crystallized from AcOEt

Sources & evidence

ORD record
ord-b9f633c7686b4f06a36e67f4d8036e9d
Source dataset
uspto-grants-1991_06
Patent number
US05021436

Reaction notes

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