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Tetrabutylammonium Fluoride → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-ethynylpyrazole

HRID 1383582
Notes
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Reaction equation

HRID 1383582 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1[C:22]#[C:23][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([O:14][C:15]([F:16])([F:18])[F:17])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1[C:22]#[CH:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 211881085-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-trimethylsilylethynylpyrazole

Product 1

HCID 211880625-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-ethynylpyrazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028
Tetrahydrofuran
Solvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-trimethylsilylethynylpyrazole (0.4657 g) in dichloromethane (5 ml) cooled in an ice-water bath was slowly added tetra-n-butylammonium fluoride (1.07 ml of a 1M solution in tetrahydrofuran). After five minutes the ice-water bath was removed. Stirring was continued for ten minutes then the reaction mixture was washed with water. The aqueous layer was washed with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to provide the title compound as an oily solid which upon drying in an oven crystallised to a white solid m.p. 175.7-176.1° C.

Workup

  1. customAfter five minutes the ice-water bath was removed
  2. waitwas continued for ten minutes
  3. washthe reaction mixture was washed with water
  4. washThe aqueous layer was washed with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-25cefb94e4ec45168a2fd37c845b32bf
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06255333B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes