Triphenylphosphine → HCID 19815323, compound

HRID 847085Notes

Reaction equation

HRID 847085 reaction equation
Br[CH2:2][C:3]1[C:4]([C:9]#[N:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:30]([C:32]1[CH:50]=[CH:49][C:35]([CH2:36][N:37]2[C:41]([CH2:42][OH:43])=[C:40]([Cl:44])[N:39]=[C:38]2[CH2:45][CH2:46][CH2:47][CH3:48])=[CH:34][CH:33]=1)=O.C[O-].[Na+]>CN(C)C=O.O>[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1/[CH:2]=[CH:30]/[C:32]1[CH:33]=[CH:34][C:35]([CH2:36][N:37]2[C:41]([CH2:42][OH:43])=[C:40]([Cl:44])[N:39]=[C:38]2[CH2:45][CH2:46][CH2:47][CH3:48])=[CH:49][CH:50]=1)#[N:10]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 895992-(Bromomethyl)benzonitrileHCID 10942334Sodium MethoxideHCID 19815283HCID 19815283, compound

Product 1

HCID 19815323HCID 19815323, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.98 g of α-bromo-o-tolunitrile in 25 mL of dimethylformamide at 25° was added 1.40 g of triphenylphosphine. The mixture was stirred at 80° for 3 hours, then treated with 1.53 g of 1-(4-formylbenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole, followed immediately by 0.54 g of sodium methoxide, and the mixture was diluted with water and extracted with benzene. The organic phases were combined and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% ethyl acetate/benzene) afforded 0.45 g of 1-[(2'-cyano-trans-stilben-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole; NMR (200 MHz, CDCl3): δ8.01 (d, 1h); 7.85 (d, 1h); 7.73 (t, 1h); 7.47 (t, 1h); 7.44 (AB, 2H, J=16.3); 7.38 (A2B2, 4H); 5.28 (s, 2H); 5.24 (t, 1H); 4.34 (d, 2H); 2.49 (t, 2H); 1.47 (quint., 2H); 1.24 (sext., 2H); 0.79 (t, 3H).

Workup

  1. extractionextracted with benzene
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06f6a3a52e154eb09a9c7a517d3a4abc
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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