Tetraethyl [[1,1'-biphenyl]-4,4'-diylbis(methylene)]bis(phosphonate) → HCID 67429302, compound

HRID 1660681Notes

Reaction equation

HRID 1660681 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]1([N:13]2[C:26]3[CH:25]=[CH:24][C:23]([CH:27]=O)=[CH:22][C:21]=3[S:20][C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OP([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([CH2:50]P(OCC)(OCC)=O)=[CH:46][CH:45]=2)=[CH:40][CH:39]=1)(=O)OCC)C>CS(C)=O>[C:7]1([N:13]2[C:26]3[CH:25]=[CH:24][C:23]([CH:27]=[CH:50][C:47]4[CH:46]=[CH:45][C:44]([C:41]5[CH:40]=[CH:39][C:38]([CH:37]=[CH:1][C:2]6[CH:5]=[CH:25][C:26]7[N:13]([C:7]8[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=8)[C:14]8[C:19]([S:20][C:21]=7[CH:3]=6)=[CH:18][CH:17]=[CH:16][CH:15]=8)=[CH:43][CH:42]=5)=[CH:49][CH:48]=4)=[CH:22][C:21]=3[S:20][C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 635132Tetraethyl [[1,1'-biphenyl]-4,4'-diylbis(methylene)]bis(phosphonate)HCID 23665647Potassium tert-butoxideHCID 86648278HCID 86648278, compound

Product 1

HCID 67429302HCID 67429302, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.73 g (24.1 mmol) of potassium tert-butoxide and then 7.80 g (25.7 mmol) of 10-phenylphenothiazine-3-carbaldehyde were added under nitrogen at room temperature with stirring to a solution of 4.83 g (10.7 mmol) of diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate in 80 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for four hours, the reaction solution was diluted with 200 ml of methanol and stirred for a further 15 min. The precipitate was filtered off, washed with 500 ml of methanol and dried at 35° C. under reduced pressure. The crude product (5.85 g) was recrystallized in 400 ml of toluene. 3.85 g of yellow solid having a melting point of 278-290° C. were obtained.

Workup

  1. customdried over molecular sieve
  2. additionthe reaction solution was diluted with 200 ml of methanol
  3. stirringstirred for a further 15 min
  4. filtrationThe precipitate was filtered off
  5. washwashed with 500 ml of methanol
  6. customdried at 35° C. under reduced pressure
  7. customThe crude product (5.85 g) was recrystallized in 400 ml of toluene
  8. customwere obtained

Sources & evidence

ORD record
ord-616823c9315c48d49335187d1b6f8b18
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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