Tert-Butyl nitrite → HCID 21188102, compound

HRID 1383611Notes

Reaction equation

HRID 1383611 reaction equation
N[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]([CH3:19])[C:3]=1[C:20]#[C:21][Si:22]([CH3:25])([CH3:24])[CH3:23].C(ON=O)(C)(C)C>O1CCCC1>[Cl:13][C:12]1[CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=[C:8]([Cl:18])[C:7]=1[N:6]1[CH:2]=[C:3]([C:20]#[C:21][Si:22]([CH3:23])([CH3:25])[CH3:24])[C:4]([CH3:19])=[N:5]1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 21188050HCID 21188050, compound

Product 1

HCID 21188102HCID 21188102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl 4-trimethylsilylethynylpyrazole (1.3 g) in tetrahydrofuran (15 ml) at 65° C. was added dropwise t-butylnitrite (1.65 g) in tetrahydrofuran (5 ml) over a period of 15 minutes and heating continued for 3 hours. The reaction mixture was left at room temperature overnight then evaporated to give the crude product as a gum which was purified by column chromatography on silica gel eluted with dichioromethane:hexane (1:1). Combination and evaporation of appropriate fractions provided the title compound as a pale yellow solid, m.p. 76-78° C.

Workup

  1. temperatureheating
  2. waitThe reaction mixture was left at room temperature overnight
  3. customthen evaporated
  4. customto give the crude product as a gum which
  5. customwas purified by column chromatography on silica gel
  6. washeluted with dichioromethane:hexane (1:1)
  7. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-184e85656ae94fadb83ca3865a98e043
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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