1,5-Dibromopentane → HCID 59624294, compound
Reaction equation
[O-:1][CH2:2][CH3:3].[Na+].O[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[C:9]#[N:10].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:21]>C(O)C>[Br:21][CH2:20][CH2:19][CH2:18][CH2:3][CH2:2][O:1][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:21])[C:9]#[N:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Another example of a diamidine derivative is a diamidine trimer having a meta-para linkage. The meta-para oligomer is synthesized by nucleophilic substitution of one bromine atom in 1,5-dibromopentane (used in large excess) by both oxygen atoms of a 3,4-dihydroxybenzonitrile sodium ethoxide containing ethanol solvent giving the 3,4-Bis-(5-bromo-pentyloxy)-benzonitrile. This benzonitrile is dissolved in ethanol and added to a solution containing 2 equivalents of 4-hydroxybenzonitrile and sodium ethoxide in ethanol providing the 3,4-Bis-[5-(4-cyano-phenoxy)-pentyloxy]-benzonitrile. Reaction of 3,4-Bis-[5-(4-cyano-phenoxy)-pentyloxy]-benzonitrile with ethanol and hydrogen chloride in toluene converts all cyano groups in the starting materials to the imidate which is isolated but not purified. The tris imidate compound is reacted with ammonia saturated ethanol to yield the desired tris amidine.
Sources & evidence
- ORD record
- ord-767efe889f634325ac70a22e4d498ad9
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436049B2
Reaction notes
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