4-Aminobenzylphosphonic acid → 1,8-Diazabicyclo(5.4.0)undec-7-ene

HRID 376528Notes

Reaction equation

HRID 376528 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][P:7](=[O:10])([OH:9])[OH:8])=[CH:4][CH:3]=1>O1CCCC1>[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][P:7](=[O:8])([OH:10])[OH:9])=[CH:4][CH:3]=1.[N:1]12[CH2:2][CH2:3][CH2:4][N:1]=[C:2]1[CH2:12][CH2:11][CH2:5][CH2:4][CH2:3]2

Participants

4

Reactant 1

HCID 2239784-Aminobenzylphosphonic acid

Product 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneYield 983.4%HCID 2239784-Aminobenzylphosphonic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A round-bottom reaction flask (25 ml) equipped with a magnetic stirrer was fitted with a septum and a cool-trap condenser. It was charged with C60 (NO2). (100 mg) and tetrahydrofuran (15 ml). The solution was added 4-aminobenzylphosphonic acid (150 mg) in tetrahydrofuran (5 ml) and treated under sonication conditions for 30 min at ambient temperatures. At the end of reaction, suspended solids in the solution were separated by a centrifuge technique and repeatedly washed with tetrahydrofuran and acetone. The resulting brown solids were dried in vacuum at 40° C. to afford the corresponding 4-aminobenzylphosphonic acid derivatives of C60, C60 [--NHC6H4CH2P(=O) (OH)3 ]n, (95 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 400 mg).

Workup

  1. customA round-bottom reaction flask (25 ml) equipped with a magnetic stirrer
  2. customwas fitted with a septum and a cool-trap condenser
  3. additionIt was charged with C60 (NO2)
  4. additiontreated under sonication conditions for 30 min at ambient temperatures
  5. customAt the end of reaction
  6. customwere separated by a centrifuge technique
  7. washrepeatedly washed with tetrahydrofuran and acetone
  8. customThe resulting brown solids were dried in vacuum at 40° C.

Sources & evidence

ORD record
ord-77845e6f2fbd4525aaccd631000ef55a
Source dataset
uspto-grants-2000_02
Patent number
US06020523

Reaction notes

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