2-Chloroethyldiisopropylammonium chloride → HCID 21293328, compound

HRID 622131Notes

Reaction equation

HRID 622131 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[N:6]=[CH:5]2.Cl.CN(C)CCCCl.Cl.C(N(C(C)C)CCCl)(C)C.[CH3:38][S:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]=[CH2:45])=[CH:42][CH:41]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C.CS(C)=O>[CH3:38][S:39][C:40]1[CH:47]=[CH:46][C:43](/[CH:44]=[CH:45]/[C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[N:6]=[CH:5]3)=[CH:42][CH:41]=1

Participants

8

Reactant 4

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 5916034-methylthiostyreneHCID 21293346HCID 21293346, compound

Product 1

HCID 21293328HCID 21293328, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

6-Bromo-2-[3-(dimethylamino)propyl]phthalazin-1(2H)-one (8.5 gm) (prepared as in Example I, except that 3-(dimethylamino)propyl chloride hydrochloride was substituted for the 2-(diisopropylamino)ethyl chloride hydrochloride) was stirred into 4 ml DMSO plus 4 ml acetonitrile. To the resulting mixture was added 3.7 gm 4-methylthiostyrene, 0.2 gm tri(O-tolyl)phosphine, and 0.04 gm palladium acetate. The reaction mixture was stirred at reflux (95°-100° C.) for 24 hours. The solution was concentrated to dryness on a rotovap and the residue recrystallized from 95% ethanol yielding 5.5 gm of product melting at 210° C.

Workup

  1. temperatureat reflux (95°-100° C.) for 24 hours
  2. concentrationThe solution was concentrated to dryness on a rotovap
  3. customthe residue recrystallized from 95% ethanol yielding 5.5 gm of product melting at 210° C.

Sources & evidence

ORD record
ord-cf54c80594a24e85b230f64f620263fd
Source dataset
uspto-grants-1988_09
Patent number
US04769369

Reaction notes

Loading…