Phosphorus oxychloride → 3-Chloro-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole

HRID 441696Notes

Reaction equation

HRID 441696 reaction equation
O[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[F:14])[N:5]=[C:4]2[CH2:15][CH2:16][S:17][CH2:18][C:3]=12.P(Cl)(Cl)([Cl:21])=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:21][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[F:14])[N:5]=[C:4]2[CH2:15][CH2:16][S:17][CH2:18][C:3]=12

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178515244HCID 178515244, compound

Product 1

HCID 214172053-Chloro-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

12.4 Parts of 3-hydroxy-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole was reacted with 6.7 parts of phosphorus oxychloride at 155° C. for 3 hours, the reaction mixture poured into 250 parts of chloroform and 250 parts of saturated aqueous NaHCO3 and stirred for 16 hours. The aqueous portion was extracted with 200 parts of chloroform, the chloroform portions combined and washed twice with 200 parts of water, dried with anhydrous magnesium sulfate, and evaporated under a reduced pressure of 50 to 300 mm Hg. to give 6.0 parts of 3-chloro-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole as a black-brown oil which when contacted with a mixture of ether and pentane changed into a light brown solid, m.p. 97°-99° C.

Workup

  1. extractionThe aqueous portion was extracted with 200 parts of chloroform
  2. washwashed twice with 200 parts of water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customevaporated under a reduced pressure of 50 to 300 mm Hg

Sources & evidence

ORD record
ord-f91e7f90c19647a4945925d6b9fbced1
Source dataset
uspto-grants-1977_08
Patent number
US04042373

Reaction notes

Loading…