O-Phenylenediamine → Benzimidazole

HRID 535221Notes

Reaction equation

[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].F[C:10](F)(F)C(F)=C(F)F>>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:10]=1

Participants

Reactant 2

HCID 7243O-Phenylenediamine

HCID 8302Hexafluoropropylene

Product 1

HCID 5798Benzimidazole

Procedure

The first step (a) illustrated on FIG. 15 is a reaction between ortho phenylene diamine 23 and hexafluoropropene 24 in autoclave for 24 hours and the resulting derived product is obtained with a good output (75%). This reaction does not make it possible to obtain a fluorinated vinyl monomer with benzimidazole functionality 21b, but to obtain 2-(1,1,1,2-tetrafluoroethyl)benzimidazole 10, after recrystallization in a water/ethanol mixture and with an output of 75%.

Workup

customis obtained with a good output (75%)

Sources & evidence

ORD record: ord-fa255fdd238f44059b99aca4c949a31f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859160B2

Reaction notes

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