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

HRID 485776Notes

Reaction equation

HRID 485776 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.S(=O)(O)[O-].[Na+].[NH2:20][C:21]1[CH:22]=[C:23]([C:34]([C:43]2[CH:48]=[CH:47][C:46]([NH:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[C:45]([NH2:56])[CH:44]=2)([C:39]([F:42])([F:41])[F:40])[C:35]([F:38])([F:37])[F:36])[CH:24]=[CH:25][C:26]=1[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O.C(O)C>[F:36][C:35]([F:37])([F:38])[C:34]([C:23]1[CH:24]=[CH:25][C:26]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:10]([C:9]3[CH:12]=[CH:13][CH:14]=[C:7]([C:6]#[CH:5])[CH:8]=3)=[N:20][C:21]=2[CH:22]=1)([C:43]1[CH:48]=[CH:47][C:46]2[N:49]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:10]([C:9]3[CH:12]=[CH:13][CH:14]=[C:7]([C:6]#[CH:5])[CH:8]=3)=[N:56][C:45]=2[CH:44]=1)[C:39]([F:40])([F:41])[F:42]

Participants

5

Reactant 3

HCID 27716423-(Trimethylsilyl)ethynylbenzaldehydeHCID 142050492,2-Bis(3-amino-4-anilinophenyl)hexafluoropropaneHCID 23665763Sodium Bisulfite

Product 1

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

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

The exact procedure described above (high dilution and dropwise addition) was repeated for 26.0 g of the aldehyde (VI), 110 g of sodium bisulfite, 30.0 g of the tetramine (V) in a total volume of 4.5 L of 1:5 water-ethanol. At the end, the powdery end product (VIII) was fractionated by Soxhlet extraction into an ether-insoluble portion (high oligomers) and an ether-soluble portion (20.0 g, 46.9%). The latter material, when tested on the Kofler hot bench at 250° C., showed a gel time of about 3 minutes.

Workup

  1. additionhigh dilution and dropwise addition)
  2. extractionAt the end, the powdery end product (VIII) was fractionated by Soxhlet extraction into an ether-insoluble portion (high oligomers)
  3. customtested on the Kofler hot bench at 250° C.
  4. customa gel time of about 3 minutes

Sources & evidence

ORD record
ord-ff917ac33cf84514945d5bf951a99ca3
Source dataset
uspto-grants-1985_08
Patent number
US04537974

Reaction notes

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