Triphenylphosphine → HCID 23076402, compound

HRID 2221662Notes

Reaction equation

HRID 2221662 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH3:10])[CH:8]=1.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[ClH:2].[Cl-:1].[CH2:9]([N:7]1[CH:8]=[C:4]([CH2:3][P+:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[N:6]1)[CH3:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 230765624-(Chloromethyl)-1-ethyl-1H-pyrazole hydrochloride

Product 1

HCID 23076402HCID 23076402, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloromethyl-1-ethyl-1H-pyrazole hydrochloride (24.00 g), triphenylphosphine (34.10 g), acetonitrile (250 mL) was heated under reflux for 16 hrs. The reaction mixture was concentrated, and the residue was decanted and washed with diethyl ether (3 times with 200 mL). Toluene was added and the mixture was concentrated under reduced pressure to give [(1-ethyl-1H-pyrazol-4-yl)methyl](triphenyl)phosphonium chloride hydrochloride as amorphous form (57.47 g, yield 95%). NMR (DMSO-d6) δ: 1.22 (3H, t, J=7.2 Hz), 4.01 (2H, q, J=7.2 Hz), 4.66 (1H,brs), 5.01 (2H, d, J=13.8 Hz), 6.93 (1H, s), 7.25 (1H, s), 7.68-7.79 (12H, m), 7.87-7.92 (3H, m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hrs
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was decanted
  5. washwashed with diethyl ether (3 times with 200 mL)
  6. additionToluene was added
  7. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af0eaadfa5df46e89af94934f84349ca
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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