Tetraethyl [[1,1'-biphenyl]-4,4'-diylbis(methylene)]bis(phosphonate) → HCID 67430310, compound

HRID 1660680Notes

Reaction equation

HRID 1660680 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][N:8]1[C:21]2[CH:20]=[CH:19][C:18]([CH:22]=O)=[CH:17][C:16]=2[S:15](=[O:25])(=[O:24])[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.C(OP([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44]([CH2:47]P(OCC)(OCC)=O)=[CH:43][CH:42]=2)=[CH:37][CH:36]=1)(=O)OCC)C>CS(C)=O.CN1CCCC1=O>[CH3:7][N:8]1[C:21]2[CH:20]=[CH:3][C:2]([CH:5]=[CH:47][C:44]3[CH:43]=[CH:42][C:41]([C:38]4[CH:37]=[CH:36][C:35]([CH:34]=[CH:22][C:18]5[CH:19]=[CH:20][C:21]6[N:8]([CH3:7])[C:9]7[C:14]([S:15](=[O:25])(=[O:24])[C:16]=6[CH:17]=5)=[CH:13][CH:12]=[CH:11][CH:10]=7)=[CH:40][CH:39]=4)=[CH:46][CH:45]=3)=[CH:1][C:16]=2[S:15](=[O:25])(=[O:24])[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

6

Reactant 3

HCID 635132Tetraethyl [[1,1'-biphenyl]-4,4'-diylbis(methylene)]bis(phosphonate)HCID 23665647Potassium tert-butoxideHCID 86648277HCID 86648277, compound

Product 1

HCID 67430310HCID 67430310, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.02 g (9.05 mmol) of potassium tert-butoxide and then 2.20 g (8.05 mmol) of 10-methyl-5,5-dioxophenothiazine-3-carbaldehyde (Example 21) were added under nitrogen at room temperature with stirring to a solution of 1.82 g (4.00 mmol) of diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate in 41 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for four hours, the reaction solution was diluted with 90 ml of methanol and stirred for a further 15 min. The precipitate was filtered off, washed with 220 ml of methanol and dried at 35° C. under reduced pressure. The crude product (2.50 g) was recrystallized in 58 ml of dimethyl sulfoxide. After solvent residues had been removed under high vacuum at 200° C., 1.64 g (59% of theory) of analytically pure yellow solid having a melting point of 360° C. were obtained, whose solution in N-methylpyrrolidone fluoresced at λ=460 nm.

Workup

  1. customdried over molecular sieve
  2. additionthe reaction solution was diluted with 90 ml of methanol
  3. stirringstirred for a further 15 min
  4. filtrationThe precipitate was filtered off
  5. washwashed with 220 ml of methanol
  6. customdried at 35° C. under reduced pressure
  7. customThe crude product (2.50 g) was recrystallized in 58 ml of dimethyl sulfoxide
  8. customAfter solvent residues had been removed under high vacuum at 200° C.
  9. customwere obtained

Sources & evidence

ORD record
ord-bbaeea5cb6e64dccaa1f79ff8b0c353f
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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