Sodium Hydroxide → HCID 178447359, compound

HRID 1609188Notes

Reaction equation

HRID 1609188 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]([CH2:23][CH2:24][O:25][CH3:26])[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=1)#[N:2].C([Sn]([N:40]=[N+:41]=[N-:42])(CCCC)CCCC)CCC.[OH-].[Na+]>CC1C=CC=CC=1C.C1(C)C=CC=CC=1>[CH3:26][O:25][CH2:24][CH2:23][N:16]([C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]2[NH:42][N:41]=[N:40][N:2]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4984872Tributyltin azideHCID 21840364HCID 21840364, compound

Product 1

HCID 178447359HCID 178447359, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 1.6 g (4.5 mmol) of crude N-[(2'-cyanobiphenyl-4-yl)methyl]-N-(2methoxyethyl)valeramide and 1.8 g (5.5 mmol) of tri-n-butyltin azide in 15 ml of o-xylene is heated under reflux for 20-24 hours while passing a gentle stream of nitrogen through. After cooling, the solution is diluted with about 30 ml of toluene, treated with 15 ml of 1N aqueous sodium hydroxide solution and intensively stirred for 2 hours. The aqueous phase is separated off and rendered acidic with 16 ml of 1N aqueous hydrochloric acid. The precipitated product is isolated by extraction with ethyl acetate. The crude title compound is thus obtained as an oil which crystallizes from a little ethyl acetate, m.p. 120°-122°.

Workup

  1. temperatureunder reflux for 20-24 hours
  2. temperatureAfter cooling
  3. customThe aqueous phase is separated off
  4. customThe precipitated product is isolated by extraction with ethyl acetate

Sources & evidence

ORD record
ord-f1d0062738124446a5d27936825696c4
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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