Diphenylphosphinic chloride → HCID 9908920, compound

HRID 1458293Notes

Reaction equation

HRID 1458293 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH:37]1[CH2:41][N:40]([CH2:42][CH3:43])[N:39]([CH2:44][CH3:45])[CH2:38]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:44]([N:39]1[CH2:38][CH:37]([NH:36][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])=[CH:20][CH:19]=2)[CH2:41][N:40]1[CH2:42][CH3:43])[CH3:45]

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 5591991,2-Diethyl-4-pyrazolidinamineHCID 123615004-Geranyloxybenzoic acid

Product 1

HCID 9908920HCID 9908920, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 4- geranyloxybenzoic acid (1.10 g) in chloroform (20 ml), triethylamine (1.11 ml) and a solution of diphenylphosphinic chloride (0.95 g) in chloroform (5 ml) were successively added. After the reaction solution was stirred for 30 minutes, 4-amino-1,2-diethylpyrazolidine (0.57 g) was added and then the mixture was stirred at room temperature for one night. The reaction solution was washed with aqueous solution of sodium hydrogencarbonate, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) and then recrystallized from n-hexane, thereby yielding 1.39 g (87%) of the aimed compound.

Workup

  1. stirringthe mixture was stirred at room temperature for one night
  2. washThe reaction solution was washed with aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated under a vacuum
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-0f04536133ba4aacbd4d438ea0cc9951
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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