Tert-Butyl nitrite → HCID 9951338, compound

HRID 1421500Notes

Reaction equation

HRID 1421500 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]#[N:20])[C:3]=1[CH:21]1[CH2:25][CH2:24][CH:23]=[CH:22]1.N(OC(C)(C)C)=O>O1CCCC1>[C:19]([C:4]1[C:3]([CH:21]2[CH2:25][CH2:24][CH:23]=[CH:22]2)=[CH:2][N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=1)#[N:20]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 9821579HCID 9821579, compound

Product 1

HCID 9951338HCID 9951338, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67.5 °C

Procedure

To 5-amino-3-cyano-4-(cyclopent-2-enyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole (300 mg, 0.77 mmol, Example 7) in dry tetrahydrofuran (THF) (8 ml ) heated at 65° C. was added dropwise tert-butyl nitrite (239 mg, 2.3 mmol) in dry THF (2 ml) over 30 min. The solution was heated for a further 3 hr at 65-70° C. The solvent was removed in vacuo and the resulting brown oil was purified by silica chromatography (eluting with DCM) to yield 170 mg of the title compound as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting brown oil was purified by silica chromatography (eluting with DCM)

Sources & evidence

ORD record
ord-0f0954d4143c4abf8d9626502bea17a2
Source dataset
uspto-grants-2000_06
Patent number
US06077859

Reaction notes

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