Sodium hydride → HCID 57305679, compound

HRID 844616Notes

Reaction equation

HRID 844616 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.P(OCC)(OCC)OCC.[C:27]([C:29]1[CH:30]=[C:31]([C:35]2C=CC=C(CP(=O)(OCC)OCC)C=2)[CH:32]=[CH:33][CH:34]=1)#[N:28].[H-].[Na+].C(C1C=C(C=CC=1)C=O)#N>COCCOC>[C:27]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=3)[CH:6]=[CH:7][CH:8]=2)[CH:32]=[CH:33][CH:34]=1)#[N:28]

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 31215Triethyl phosphiteHCID 90670m-FormylbenzonitrileHCID 154275313′-(Bromomethyl)[1,1′-biphenyl]-3-carbonitrileHCID 22613922HCID 22613922, compound

Product 1

HCID 57305679HCID 57305679, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5.0 g of 3′-bromomethylbiphenyl-3-carbonitrile and 5 ml of triethyl phosphite are mixed together and slowly heated to 150°. The mixture is stirred at 150° for 6 h and after customary working up 6.05 g of diethyl 3′-cyanobiphenyl-3-ylmethylphosphonate (“BA”) are obtained. 150 mg of sodium hydride are added with ice-cooling and under nitrogen to a solution of 1.0 g of “BA” and 3-cyanobenzaldehyde in 20 ml of ethylene glycol dimethyl ether. The mixture is stirred for 4 hours, worked up in the customary manner and 0.93 g of 3′-[2-(3-cyanophenyl)vinyl]biphenyl-3-carbonitrile (“BB”) is obtained. After hydrogenation of 360 mg of “BB” with Pd-C, 5% in methanol, 360 mg of 3′-[2-(3-cyanophenyl)ethyl]biphenyl-3-carbonitrile (“DC”) are obtained. After reaction with hydroxylammonium chloride and hydrogenation with Raney nickel, the compound 3,-[2-(3-amidinophenyl)ethyl]biphenyl-3-carboxamidine, FAB 343

Workup

  1. temperatureslowly heated to 150°
  2. customare obtained
  3. stirringThe mixture is stirred for 4 hours

Sources & evidence

ORD record
ord-d9fd84137fad4ecca652929e6f201d13
Source dataset
uspto-grants-2002_04
Patent number
US06380430B1

Reaction notes

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