Sodium Pyrosulfite → 5,5'-(Hexafluoroisopropylidene)bis[1-phenyl-2-(3-ethynylphenyl)benzimidazole]

HRID 279922Notes

Reaction equation

HRID 279922 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O)(C)C.[NH2:15][C:16]1[CH:17]=[C:18]([C:29]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[C:40]([NH2:51])[CH:39]=2)([C:34]([F:37])([F:36])[F:35])[C:30]([F:33])([F:32])[F:31])[CH:19]=[CH:20][C:21]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)C.O.C(O)C.Cl>[F:31][C:30]([F:32])([F:33])[C:29]([C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]([C:9]3[CH:12]=[CH:13][CH:14]=[C:7]([C:6]#[CH:5])[CH:8]=3)=[N:15][C:16]=2[CH:17]=1)([C:38]1[CH:43]=[CH:42][C:41]2[N:44]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:10]([C:9]3[CH:12]=[CH:13][CH:14]=[C:7]([C:6]#[CH:5])[CH:8]=3)=[N:51][C:40]=2[CH:39]=1)[C:34]([F:35])([F:36])[F:37]

Participants

7

Reactant 3

HCID 656671Sodium PyrosulfiteHCID 27716423-(Trimethylsilyl)ethynylbenzaldehyde2×HCID 142050492,2-Bis(3-amino-4-anilinophenyl)hexafluoropropane2×

Product 1

HCID 233229675,5'-(Hexafluoroisopropylidene)bis[1-phenyl-2-(3-ethynylphenyl)benzimidazole]

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

Compound VIII was synthesized from compounds (VI) and (V) as follows. A mixture of 2.00 g of sodium metabisulfite and 0.76 g (4.26 mmol) of 3-(trimethylsilylethynyl)benzaldehyde (VI) in 50 ml of 1:1 ethanol-water was deaerated with argon and heated at 75°-80° C. for 30 minutes. The yellow solution was then treated with a slurry of 1.00 g (1.94 mmol) of 2,2-bis(3-amino-4-anilinophenyl)hexafluoropropane (V) in 50 ml of ethanol. The mixture was heated at a gentle reflux (oil bath temperature about 100° C.) for 7 hours, cooled, diluted with 100 ml of 10% hydrochloric acid. The bright yellow solid was filtered, then washed with 50 ml of 10% hydrochloric acid, 50 ml of water and 50 ml of cold hexane. The powdery product (VII), after thorough drying, weighed 1.67 g (1.90 mmol, 97.8%) and showed characteristic trimethylsilylethynyl absorptions in its infrared spectrum.

Workup

  1. temperatureheated at 75°-80° C. for 30 minutes
  2. temperatureThe mixture was heated at
  3. temperaturecooled
  4. filtrationThe bright yellow solid was filtered
  5. washwashed with 50 ml of 10% hydrochloric acid, 50 ml of water and 50 ml of cold hexane

Sources & evidence

ORD record
ord-9bb484e2b34743d2a12333701c84957e
Source dataset
uspto-grants-1986_05
Patent number
US04587315

Reaction notes

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