(Diethylamino)sulfur trifluoride → HCID 9924669, compound

HRID 861245Notes

Reaction equation

HRID 861245 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH2:19]O)[C:3]=1[C:21]#[N:22].C(N(S(F)(F)[F:29])CC)C>ClCCl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH2:19][F:29])[C:3]=1[C:21]#[N:22]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22618369HCID 22618369, compound

Product 1

HCID 9924669HCID 9924669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxymethylpyrazole (1.25 g) in dichloromethane (10 ml) was added slowly to a stirred solution of diethylaminosulphur trifluoride (0.66 g) in dichloromethane (6 ml) cooled to -78° C. After 30 minutes at this temperature the solution was warmed to room temperature and stirred for 2 hours. The mixture was then poured onto water (20 ml) and the dichloromethane layer was separated, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. The product was purified by chromatography on silica (Merck, 40°-230 mesh, 0.7 kg cm-2) eluting with a mixture of dichloromethane and ethyl acetate (98:2), and subsequent recrystallization from dichloromethane-petroleum ether to give 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-fluoromethylpyrazole as a white solid m.p. 139°-141° C.

Workup

  1. temperatureAfter 30 minutes at this temperature the solution was warmed to room temperature
  2. additionThe mixture was then poured onto water (20 ml)
  3. customthe dichloromethane layer was separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe product was purified by chromatography on silica (Merck, 40°-230 mesh, 0.7 kg cm-2)
  8. washeluting with a mixture of dichloromethane and ethyl acetate (98:2), and subsequent recrystallization from dichloromethane-petroleum ether

Sources & evidence

ORD record
ord-a8d7f5f9f39946c9abc4e7354113ec63
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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