10-Methyl-10H-phenothiazine-3-carbaldehyde → HCID 67431933, compound

HRID 1660679Notes

Reaction equation

HRID 1660679 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][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.C(OP([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45]P(OCC)(OCC)=O)=[CH:41][CH:40]=2)=[CH:35][CH:34]=1)(=O)OCC)C>CN1CCCC1=O>[CH3:7][N:8]1[C:21]2[CH:20]=[CH:3][C:2]([CH:5]=[CH:45][C:42]3[CH:41]=[CH:40][C:39]([C:36]4[CH:35]=[CH:34][C:33]([CH:32]=[CH:22][C:18]5[CH:19]=[CH:20][C:21]6[N:8]([CH3:7])[C:9]7[C:14]([S:15][C:16]=6[CH:17]=5)=[CH:13][CH:12]=[CH:11][CH:10]=7)=[CH:38][CH:37]=4)=[CH:44][CH:43]=3)=[CH:1][C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

5

Reactant 3

HCID 61782610-Methyl-10H-phenothiazine-3-carbaldehydeHCID 635132Tetraethyl [[1,1'-biphenyl]-4,4'-diylbis(methylene)]bis(phosphonate)HCID 23665647Potassium tert-butoxide

Product 1

HCID 67431933HCID 67431933, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.80 g (7.1 mmol) of potassium tert-butoxide and then 1.82 g (3.3 mmol) of 10-methylphenothiazine-3-carbaldehyde were added under nitrogen at room temperature with stirring to a solution of 1.42 g (3.14 mmol) of diethyl[4′-(diethoxyphosphoryl-methyl)biphenyl-4-ylmethyl]phosphonate (U.S. Pat. No. 3,984,399, Example 2, column 29, line 58-66) in 32 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for four hours, the reaction solution was diluted with 70 ml of methanol and stirred for a further 15 min. The precipitate was filtered off, washed with 172 ml of methanol and dried at 35° C. under reduced pressure. The crude product (1.70 g) was recrystallized in 255 ml of N-methylpyrrolidone. After the solvent residues had been removed at 225° C. under high vacuum, 0.98 g (50% of theory) of analytically pure yellow solid having a melting point of 380° C. was obtained, whose solution in N-methylpyrrolidone fluoresced at λ=576 nm.

Workup

  1. dry with material3,984,399, Example 2, column 29, line 58-66) in 32 ml of dimethyl sulfoxide dried over molecular sieve
  2. additionthe reaction solution was diluted with 70 ml of methanol
  3. stirringstirred for a further 15 min
  4. filtrationThe precipitate was filtered off
  5. washwashed with 172 ml of methanol
  6. customdried at 35° C. under reduced pressure
  7. customThe crude product (1.70 g) was recrystallized in 255 ml of N-methylpyrrolidone
  8. customAfter the solvent residues had been removed at 225° C. under high vacuum, 0.98 g (50% of theory) of analytically pure yellow solid
  9. customwas obtained

Sources & evidence

ORD record
ord-a646f96522d044abbcfc5ecba75467c6
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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