HCID 20232011, compound → HCID 15586410, compound

HRID 2290363Notes

Reaction equation

HRID 2290363 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([NH:14][NH2:15])=[N:10][C:9]=2[CH3:16])=[CH:4][CH:3]=1.ICS[C:20]1[NH:21][CH2:22][CH2:23][N:24]=1>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[N:12][C:11]([NH:14][NH:15][C:20]3[NH:24][CH2:23][CH2:22][N:21]=3)=[N:10][C:9]=2[CH3:16])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 20232011HCID 20232011, compoundHCID 20232073HCID 20232073, compound

Product 1

HCID 15586410HCID 15586410, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6-(4-chlorophenyl)-3-hydrazino-5-methyl-1,2,4-triazine (7 g), 2-iodomethylthio-2-imidazoline (8.11 g) and n-butanol (50 ml) was refluxed for 3 hours with stirring. After cooling, the mixture was evaporated under reduced pressure and the residue was dissolved in 1N hydrochloric acid. The solution was washed with ethyl acetate and made alkaline with an aqueous solution of potassium carbonate. The resultant precipitates were collected by filtration, washed with water, dried and recrystallized from methanol and then from ethanol to give dark red crystals of 6-(4-chlorophenyl)-3-[2-(2-imidazolin-2-yl)hydrazino]-5-methyl-1,2,4-triazine (1.53 g), m.p. 230°~231° C. (decomp.).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in 1N hydrochloric acid
  5. washThe solution was washed with ethyl acetate
  6. customThe resultant precipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-62ab3297fbc64afdbb932da8de2854f1
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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