Isoamyl Nitrite → HCID 18668822, compound

HRID 1058567Notes

Reaction equation

HRID 1058567 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17](N)=[C:16]([C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[C:15]([S:25][CH3:26])=[N:14]1.N(OCCC(C)C)=O>CN(C=O)C.C(OCC)C>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[CH:17]=[C:16]([C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[C:15]([S:25][CH3:26])=[N:14]1

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 18668835HCID 18668835, compound

Product 1

HCID 18668822HCID 18668822, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of aminopyrazole 41 (42 mg, 0.1 mmol) in DMF (5 mL) was warmed up to 65° C. and treated dropwise with excess isoamyl nitrite (150 mL). Stirring was continued for 30 min. The reaction was cooled down to room temperature, diluted with ethyl ether (10 mL) and washed with brine (5×15 mL). The organic layer was dried (magnesium sulfate) and the solvents removed at reduced pressure, leaving a dark oil residue. The desired product was obtained upon flash chromatography eluting with ethyl acetate-hexanes (5-10%), to yield 14 mg (35%) of desired product. 1H-NMR (δ, CDCl3): 2.63 (3H, s); 7.78 (2H, s); 8.1 (1H, s); 8.28 (1H, d, J=2.5 Hz); 8.4 (1H, dd, J=1.4; 8.4 Hz); 9.2 (1H, d, J=1.5 Hz). MS: M+1=404 (calculated: 404).

Workup

  1. washwashed with brine (5×15 mL)
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. customthe solvents removed at reduced pressure
  4. customleaving a dark oil residue

Sources & evidence

ORD record
ord-fcf26098e7664bafbfe653932d3fb040
Source dataset
uspto-grants-2003_02
Patent number
US06518266B1

Reaction notes

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