Thionyl Chloride → HCID 13281458, compound

HRID 1249122Notes

Reaction equation

HRID 1249122 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[C:13]=2[Cl:20])[C:7]=1[NH:8][CH2:9][CH2:10]O)#[N:2].S(Cl)([Cl:23])=O>>[Cl:23][CH2:10][CH2:9][NH:8][C:7]1[N:6]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[C:13]=2[Cl:20])[N:5]=[CH:4][C:3]=1[C:1]#[N:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13281457HCID 13281457, compound

Product 1

HCID 13281458HCID 13281458, compound

Procedure

A solution of 4-cyano-5-(2-hydroxyethyl)amino-1-(2,3,4-trichlorophenyl)pyrazole (3.0 g; prepared as described in Example 27) in thionyl chloride (25 ml) was heated under reflux for 5 hours. The solution was evaporated under reduced pressure and the residue was dissolved in dichloromethane (100 ml). The dichloromethane solution was washed with water (2×200 ml), dried over anhydrous magnesium sulphate and evaporated to give an orange gum, whicn was chromatographed using dichloromethane as eluent. Evaporation of the eluate containing the major component gave 5-(2-chloroethyl)amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 125°-128° C., in the form of a cream-coloured solid.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solution was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (100 ml)
  4. washThe dichloromethane solution was washed with water (2×200 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. customto give an orange gum, whicn
  8. customwas chromatographed
  9. customEvaporation of the eluate
  10. additioncontaining the major component

Sources & evidence

ORD record
ord-5f26b034127244cc9389f440de289754
Source dataset
uspto-grants-1986_12
Patent number
US04629495

Reaction notes

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