Sodium Hydroxide → HCID 178425460, compound

HRID 486478Notes

Reaction equation

HRID 486478 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.NC(N)=[S:23].[OH-].[Na+]>>[CH3:20][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:4]=[N:3][C:2]([SH:23])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 15124568HCID 15124568, compound

Product 1

HCID 178425460HCID 178425460, compoundYield 22.7%

Conditions

Temperature
165 °C

Procedure

A mixture of 5.8 parts of 3-chloro-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine and 3 parts of thiourea was stirred for 3 hours in an oil bath at 165° C. After cooling, there were added 150 parts of a sodium hydroxide solution 0.5N. The whole was stirred and refluxed for 15 minutes. It was filtered while hot and the filtrate was neutralized with acetic acid. The product was filtered off, washed with water and separated by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of ethanol and tetrahydrofuran. The product was filtered off and dried, yielding 1.3 parts (22.7%) of 6-[4-(3-methylphenyl)-1-piperazinyl]-3-pyridazinethiol; mp. 174.2° C. (compound 273).

Workup

  1. temperatureAfter cooling
  2. stirringThe whole was stirred
  3. temperaturerefluxed for 15 minutes
  4. filtrationIt was filtered while hot and the filtrate
  5. filtrationThe product was filtered off
  6. washwashed with water
  7. customseparated by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of ethanol and tetrahydrofuran
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-d617196f540a407ba41afb5073c1ef09
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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