Sodium Hydroxide → HCID 178457034, compound

HRID 2380681Notes

Reaction equation

HRID 2380681 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:28][CH2:29][CH3:30])[C:17](=[O:27])[C:18]2[CH:26]=[CH:25][CH:24]=[C:20]([C:21]([OH:23])=[O:22])[CH:19]=2)=[CH:11][CH:10]=1)#[N:2].C([Sn]([N:44]=[N+:45]=[N-:46])(CCCC)CCCC)CCC.[OH-].[Na+].C(Cl)Cl.CO>C1(C)C(C)=CC=CC=1>[CH2:28]([N:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]2[NH:46][N:45]=[N:44][N:2]=2)=[CH:14][CH:13]=1)[C:17](=[O:27])[C:18]1[CH:26]=[CH:25][CH:24]=[C:20]([C:21]([OH:23])=[O:22])[CH:19]=1)[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 4984872Tributyltin azideHCID 21226129Dichloromethane methanolHCID 54327068N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-isophthalic acid monoamide

Product 1

HCID 178457034HCID 178457034, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2.76 g of N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-isophthalic acid monoamide and 8.68 g of tributyltin azide in 75 ml of xylene is heated under reflux for 2 hours. When cool, the mixture is stirred with 50 ml of 2N sodium hydroxide solution at room temperature for 1 hour, and is then acidified and extracted with 100 ml and twice with 50 ml of CH2Cl2. After customary treatment, the combined dichloromethane phases yield a crude product that, after chromatography on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (9:1) as eluant, yields N-propyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-isophthalic acid monoamide that has an Rf value of 0.10 [CH2Cl2 /CH3OH (4:1)]. ##STR10##

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureWhen cool
  3. extractionextracted with 100 ml and twice with 50 ml of CH2Cl2
  4. customAfter customary treatment, the combined dichloromethane phases yield a crude product that

Sources & evidence

ORD record
ord-80708ffc3cd846fb8fc4fbb3682a9aa2
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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