Tert-Butyl nitrite → HCID 21188074, compound

HRID 1383604Notes

Reaction equation

HRID 1383604 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]([C:19]([F:22])([F:21])[F:20])[C:3]=1[C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26].C(ON=O)(C)(C)C>O1CCCC1>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[CH:2]=[C:3]([C:23]#[C:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:4]([C:19]([F:22])([F:21])[F:20])=[N:5]1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 21188087HCID 21188087, compound

Product 1

HCID 21188074HCID 21188074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethyl4-trimethylsilylethynylpyrazole (6.39 g) in tetrahydrofuran (50 ml) at 65° C. was added dropwise over one hour t-butylnitrite (7.15 g) in tetrahydrofuran (10 ml). Heating was continued for 2 hours then the mitue was left at room temperature overnight. After evaporation the residue was taken up in hexane and decanted free from insoluble materials. The solution was evaporated and the residue purified by column chromatography on silica gel eluted with dichloromethane:hexane (1:1). Combination and evaporation of appropriate fractions, followed by recrystallisation from hexane, provided the title compound as a pale yellow solid, m.p. 105-108° C.

Workup

  1. temperatureHeating
  2. waitthe mitue was left at room temperature overnight
  3. customAfter evaporation the residue
  4. customdecanted free from insoluble materials
  5. customThe solution was evaporated
  6. customthe residue purified by column chromatography on silica gel
  7. washeluted with dichloromethane:hexane (1:1)
  8. customCombination and evaporation of appropriate fractions
  9. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-61e89d9acb4c4d7487fb2d50d9da66e6
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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