Thionyl Chloride → HCID 14989395, compound

HRID 1030944Notes

Reaction equation

HRID 1030944 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH2:15][O:16][C:17]3[CH:28]=[CH:27][C:20]([C:21]([NH:23][CH2:24][CH2:25]O)=[O:22])=[CH:19][CH:18]=3)(O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:28]=[CH:27][C:20]([C:21]4[O:22][CH2:25][CH2:24][N:23]=4)=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14989394HCID 14989394, compound

Product 1

HCID 14989395HCID 14989395, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred and cooled mixture of 10 parts of 4-[[1-(6-chloro-3-pyridazinyl)-4-hydroxy-4-piperidinyl]methoxy]-N-(2-hydroxyethyl)benzamide and 228 parts of ethyl acetate were added dropwise 8.4 parts of thionyl chloride. Upon complete addition, stirring was continued first overnight at room temperature and then for 1 hour at 60° C. The reaction mixture was evaporated and the residue was dissolved in a solution of 20 parts of sodium hydrogen carbonate in 160 parts of ethanol. The whole was stirred overnight at reflux temperature. After evaporation, the residue was taken up in water. The precipitated product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 1 part (10.7%) of 3-chloro-6-[4-[[4-(4,5-dihydro-2-oxazolyl)phenoxy]methyl]-3,6-dihydro-1(2H)-pyridinyl]pyridazine; mp. 176.0° C. (comp. 168).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. waitfor 1 hour at 60° C
  5. customThe reaction mixture was evaporated
  6. dissolutionthe residue was dissolved in a solution of 20 parts of sodium hydrogen carbonate in 160 parts of ethanol
  7. stirringThe whole was stirred overnight
  8. temperatureat reflux temperature
  9. customAfter evaporation
  10. filtrationThe precipitated product was filtered off
  11. custompurified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from 2-propanol
  16. filtrationThe product was filtered off
  17. customdried

Sources & evidence

ORD record
ord-1c606e59d071414c8e70a26867f55348
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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