Isoamyl Nitrite → HCID 9819252, compound

HRID 1265178Notes

Reaction equation

HRID 1265178 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]2[CH2:19][S:20][CH2:21][C:15]2=[N:14]1.N(OCCC(C)C)=O>CN(C=O)C>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[CH:17]=[C:16]2[CH2:19][S:20][CH2:21][C:15]2=[N:14]1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 9798660HCID 9798660, compound

Product 1

HCID 9819252HCID 9819252, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4,6-dihydrothieno-[3,4-c]pyrazole-3-ylamine (200 mg, 0.56 mmol) in DMF (5 mL) is warmed up to 65° C. and isoamyl nitrite (0.3 mL) was added dropwise and the reaction mixture stirred for 1 h at the same temperature. After cooling to room temperature, the mixture was extracted with ethyl ether (50 mL) and washed with brine (4×25 mL). After drying the organic phase (MgSO4), volatile materials were removed under reduced pressure, and the residue was subjected to flash chromatography on silica, (10% ethyl acetate:hexanes). The product was recrystallized (hexane) and obtained in 76% yield. 1H NMR (CDCl3) δ 7.72 (s, 2H), 4.01 and 4.09 (m, 2H each); MS (M+) 339.

Workup

  1. extractionthe mixture was extracted with ethyl ether (50 mL)
  2. washwashed with brine (4×25 mL)
  3. dry with materialAfter drying the organic phase (MgSO4), volatile materials
  4. customwere removed under reduced pressure
  5. customThe product was recrystallized (hexane)
  6. customobtained in 76% yield

Sources & evidence

ORD record
ord-c4d838415ffd48ef9adccd55f7c761ea
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

Loading…