Hydrazine → 4'-[(3,5-Dibutyl-1h-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylic acid, hydrazide

HRID 719545Notes

Reaction equation

HRID 719545 reaction equation
[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([O:29]C)=O)=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[NH2:31][NH2:32]>CO>[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([NH:31][NH2:32])=[O:29])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 10319113methyl 4'-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylate

Product 1

HCID 100698694'-[(3,5-Dibutyl-1h-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylic acid, hydrazideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 7.10 g (17.5 mmol) sample of the methyl ester product compound of Example 1 was dissolved in 150 ml of methanol and treated with 22 ml (22.2 g 695 mmol) of anhydrous hydrazine under a static nitrogen atmosphere. The reaction was stirred at reflux for 2 days and concentrated in vacuo to give 7.03 g (99%) of compound which was a colorless glass: NMR (CDCl3) δ 0.88 (t, J=7 Hz, 3H), 0.94 (t, J=7 Hz, 3H), 1.28–1.47 (m, 4H), 1.62–1.78 (m, 4H), 2.62–2.73 (m, 4H), 3.5–4.1 (br s, 2H), 5.26 (s, 2H), 6.53 (s, 1H), 7.13–7.63 (m, 8H).

Workup

  1. temperatureat reflux for 2 days
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39b2051353114bec8136bfdd0b2ebb99
Source dataset
uspto-grants-2006_11
Patent number
US07132437B2

Reaction notes

Loading…