Water → 1-[Bis(dimethylamino)phosphinyl]-2-cyano-4-(2,4-dichlorophenyl)imidazole

HRID 727824Notes

Reaction equation

HRID 727824 reaction equation
[C:1]([C:3]1[NH:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:7]=1)#[N:2].[H-].[Na+].[CH3:18][N:19]([CH3:26])[P:20](Cl)([N:22]([CH3:24])[CH3:23])=[O:21].O>O1CCCC1>[CH3:18][N:19]([P:20]([N:22]([CH3:24])[CH3:23])([N:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:7]=[C:3]1[C:1]#[N:2])=[O:21])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74150N,N,N',N'-Tetramethylphosphorodiamidic chlorideHCID 178510565HCID 178510565, compound

Product 1

HCID 198251441-[Bis(dimethylamino)phosphinyl]-2-cyano-4-(2,4-dichlorophenyl)imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-cyano-4-(2,4-dichlorophenyl)imidazole (1.0 g) in tetrahydrofuran (30 ml) was treated with sodium hydride (0.16 g of 80% dispersion in oil) at 0°. A solution of tetramethylphosphorodiamidic chloride (0.89 g) in tetrahydrofuran (10 ml) was added dropwise and the mixture stirred for 11/2 hours under nitrogen. It was then poured into water, stirred, and the precipitate filtered, dried and recrystalllsed from toluene/hexane to give 1-[bis(dimethylamino)phosphinyl]-2-cyano-4-(2,4-dichlorophenyl)imidazole, m.p. 140.5°-1°. (Compound 6).

Workup

  1. stirringstirred
  2. filtrationthe precipitate filtered
  3. customdried

Sources & evidence

ORD record
ord-518852623cd1434a8a514a92090da72c
Source dataset
uspto-grants-1991_09
Patent number
US05045557

Reaction notes

Loading…