Benzaldehyde → HCID 77879496, compound

HRID 1447814Notes

Reaction equation

HRID 1447814 reaction equation
[CH3:1][Sn:2]([CH3:10])([CH3:9])[CH2:3][CH2:4][C:5]([NH:7][NH2:8])=[O:6].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[C:12]1([CH:11]=[N:8][NH:7][C:5](=[O:6])[CH2:4][CH2:3][Sn:2]([CH3:10])([CH3:9])[CH3:1])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 12901376HCID 12901376, compound

Product 1

HCID 77879496HCID 77879496, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the manner described in Example 2, 3.0 g (0.012 mole) of 3-trimethylstannylpropionic acid hydrazide was reacted with 1.5 ml (0.015 mole) of benzaldehyde in 2.0 ml of ethanol. Recrystallization of the solid product from 95% ethanol gave 3.6 g of 3-trimethylstannylpropionic acid phenylmethylenehydrazide, Compound 3 of Table I. The infrared spectrum (KBr disc) showed N--H absorptions at 3100 cm-1 and a carbonyl band at 1670 cm-1. The carbon-tin bond gave characteristic absorptions at 770, 540, 520 and 505 cm-1. NMR spectroscopy (CDCl3) showed the following: the singlet at 10.43 delta (1H, N--H); a broadened singlet at 7.87 delta (1H, -N=CHPh); the aromatic protons formed two complex bands, 2H ortho centered at 7.64 delta and 3H meta and para centered at 7.38 delta; a triplet centered at 2.99 delta (2H, COCH2); a triplet centered at 1.11 delta (2H, SnCH2); and a singlet at the 0.14 delta (9H, Sn(CH3)3) flanked by the J(117/119Sn--CH3) doublets.

Workup

  1. customRecrystallization of the solid product from 95% ethanol

Sources & evidence

ORD record
ord-5c84f00ddf654c39a0433d9e924bdf32
Source dataset
uspto-grants-1979_12
Patent number
US04178382

Reaction notes

Loading…