Hydrazine hydrate (1:1) → HCID 178469319, compound

HRID 543136Notes

Reaction equation

HRID 543136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[N:27][C:28]#[N:29])SC)=[C:9]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].O.[NH2:36][NH2:37]>C(O)C>[NH2:29][C:28]1[N:27]=[C:24]([NH:23][CH2:22][CH2:21][O:20][CH2:19][C:10]2[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:37][N:36]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178469320HCID 178469320, compound

Product 1

HCID 178469319HCID 178469319, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{2-[(4-{2-Chlorophenyl}-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl)methoxy]ethyl}-N'-cyano-S-methyl-isothiourea (0.4 g) and hydrazine hydrate (0.15 ml) were dissolved in ethanol (20 ml) and heated under reflux for 3 hours. The solvent was then evaporated and toluene (10 ml) was added to the residue, and again the solution was evaporated to dryness. The residue was chromatographed on Merck "Kieselgel 60H" (Trade Mark), eluting with 2% methanol in methylene chloride, to give a beige solid. The solid was recrystallised from ethyl acetate plus a trace of ether to give the title compound, yield 0.1 g, m.p. 137°-138°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was then evaporated
  4. additiontoluene (10 ml) was added to the residue
  5. customagain the solution was evaporated to dryness
  6. customThe residue was chromatographed on Merck "Kieselgel 60H" (Trade Mark)
  7. washeluting with 2% methanol in methylene chloride
  8. customto give a beige solid
  9. customThe solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-5469f32c1ab749628d0a5e750a84e5b6
Source dataset
uspto-grants-1987_04
Patent number
US04661485

Reaction notes

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