(Diethylamino)sulfur trifluoride → HCID 9924669, compound

HRID 2253781Notes

Reaction equation

HRID 2253781 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-9a56e1f5c869468a95153ffe01769a33
Source dataset
uspto-grants-1993_08
Patent number
US05232940

Reaction notes

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