N,N-Dimethylbenzylamine → HCID 54190960, compound

HRID 2073649Notes

Reaction equation

HRID 2073649 reaction equation
Cl[C:2]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1)=O.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=C)=[CH:17][CH:16]=1.C(N(C)C)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC(C)=CC=1>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH:2][C:4]2[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7681N,N-DimethylbenzylamineHCID 162634-BromostyreneHCID 53717999HCID 53717999, compound

Product 1

HCID 54190960HCID 54190960, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

2.13 g (11.1 mmols) of 4-chloroformylcinnamonitrile, 2.24 g (11.1 mmols) of 4-bromostyrene, 1.51 g (11.1 mmols) of N-benzyldimethylamine and 0.0246 g (0.11 mmol) of palladium acetate are added under argon to 30 ml of p-xylene, and the reaction mixture is stirred at 130° C. for 1.5 hours. The crude product which has been precipitated is filtered off at room temperature and is recrystallised from methanol and then from carbon tetrachloride. 0.38 g (11% of theory) of 4-bromostilbene-4'-acrylonitrile are obtained; melting point 258° C.

Workup

  1. customThe crude product which has been precipitated
  2. filtrationis filtered off at room temperature
  3. customis recrystallised from methanol

Sources & evidence

ORD record
ord-dd9dda0736a445139a20c2ce205b6346
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

Loading…