Diethyl benzhydrylphosphonate → 3,7-Bis(2,2-diphenylvinyl)-10-phenylphenothiazine

HRID 1660678Notes

Reaction equation

HRID 1660678 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]=[C:17]([CH:29]=O)[CH:18]=3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:31](P(=O)(OCC)OCC)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:2]1([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:27][C:23]2[CH:24]=[CH:25][C:26]3[N:13]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:14]4[C:19]([S:20][C:21]=3[CH:22]=2)=[CH:18][C:17]([CH:29]=[C:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:16][CH:15]=4)[CH:3]=[CH:19][CH:14]=[CH:15][CH:1]=1

Participants

4

Reactant 3

HCID 10267017Diethyl benzhydrylphosphonateHCID 23665647Potassium tert-butoxideHCID 5960963510-Phenylphenothiazine-3,7-dicarbaldehyde

Product 1

HCID 596096153,7-Bis(2,2-diphenylvinyl)-10-phenylphenothiazine

Procedure

6.63 g (58.1 mmol) of potassium tert-butoxide and then 8.50 g (25.7 mmol) of 10-phenylphenothiazine-3,7-dicarbaldehyde were added at room temperature with stirring to a solution of 15.61 g (51.3 mmol) of diethyl benzhydrylphosphonate (prepared analogously to Example 13 in U.S. Pat. No. 5,130,603) in 121 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for 5 hours, the reaction solution was diluted with 1500 ml of methanol and stirred for a further 15 min. The precipitate was filtered off, washed with methanol and dried at 80° C. under reduced pressure. 6.92 g (43% of theory) of yellowish solid having a melting point of 232-237° C. were obtained.

Workup

  1. customprepared analogously to Example 13 in U.S
  2. dry with material5,130,603) in 121 ml of dimethyl sulfoxide dried over molecular sieve
  3. additionthe reaction solution was diluted with 1500 ml of methanol
  4. stirringstirred for a further 15 min
  5. filtrationThe precipitate was filtered off
  6. washwashed with methanol
  7. customdried at 80° C. under reduced pressure
  8. customwere obtained

Sources & evidence

ORD record
ord-a9d196f96d29410e8f8136439c0d4ad2
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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