Sodium Methoxide → HCID 86602383, compound

HRID 857818Notes

Reaction equation

HRID 857818 reaction equation
C[O-].[Na+].[C:4]1([CH3:26])[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[C:27]1([CH3:56])[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]([C:41]1[CH:55]=[CH:54][C:44]([CH2:45]P(=O)(OCC)OCC)=[CH:43][CH:42]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40]>CN(C=O)C>[C:4]1([CH3:26])[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:18]1[CH:25]=[CH:24][C:21](/[CH:22]=[CH:45]/[C:44]2[CH:43]=[CH:42][C:41]([N:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH3:56])=[CH:55][CH:54]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 22251507HCID 22251507, compoundHCID 86602382HCID 86602382, compound

Product 1

HCID 86602383HCID 86602383, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Sodium methoxide (4.9 mmol) was added to a stirring solution of 4-(N,N-di-tolylamino)benzaldehyde (3.78 mmol) and diethyl 4-(N,N-di-tolylamino)-benzylphosphonate (3.78 mmol) in 15 mL of DMF at 25° C. The mixture stirred for 4 h at 25° C., producing a yellow precipitate. The solid was collected, and then slurried in warm water. The solid was collected again, and crystallized from ethanol/toluene to yield 1.5 g of the stilbene, (E)-4,4′-bis-(N,N-di-tolylamino)stilbene (Inv-5). H1 NMR and mass spectra data were consistent with the structure.

Workup

  1. customproducing a yellow precipitate
  2. customThe solid was collected
  3. customThe solid was collected again
  4. customcrystallized from ethanol/toluene

Sources & evidence

ORD record
ord-c319c33a4829421f80ceee27bb87fb10
Source dataset
uspto-grants-2006_12
Patent number
US07147938B2

Reaction notes

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