Diphenylmethane → HCID 57269183, compound

HRID 726530Notes

Reaction equation

HRID 726530 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1Cl)([O-:3])=[O:2].C1(CC2C=CC=CC=2)C=CC=CC=1.[CH2:31]([O:33][P:34]([CH2:39][NH2:40])(=[O:38])[O:35][CH2:36][CH3:37])[CH3:32]>C(Cl)Cl>[CH2:31]([O:33][P:34]([CH2:39][NH:40][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:38])[O:35][CH2:36][CH3:37])[CH3:32]

Participants

5

Reactant 3

HCID 7580DiphenylmethaneHCID 169871-Chloro-2,4-dinitronaphthaleneHCID 1596920Diethyl (aminomethyl)phosphonate

Product 1

HCID 57269183HCID 57269183, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g of 2,4 dinitro-1-chloronaphthalene (15.84 mmol) is dissolved in 6.5 g of aminomethanephosphonic acid diethyl ester and 4 g of diphenylmethane and stirred for 72 hours at room temperature. The batch is diluted with methylene chloride, washed with 1N NaOH and washed twice with brine, dried and spun in. The crude product is chromatographed on silica gel with 3.5 liters of cyclohexane and ethyl acetate 1:1 as mobile solvent. 68% of product is obtained in several fractions as viscous oil. NMR (DMSO, delta in ppm): 1.15(6H,tr), 4(4H dq)4.25 (2H m), 7.8, 7.98, 8.9, 9.05 each 1H, 8.6 (2H,d)

Workup

  1. washwashed with 1N NaOH
  2. washwashed twice with brine
  3. customdried
  4. customThe crude product is chromatographed on silica gel with 3.5 liters of cyclohexane and ethyl acetate 1:1 as mobile solvent

Sources & evidence

ORD record
ord-6e89d2b9eb18404d827b73c639cdde4c
Source dataset
uspto-grants-1998_01
Patent number
US05710138

Reaction notes

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