Triphenylphosphine → [5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethane-nitrile

HRID 49271Notes

Reaction equation

HRID 49271 reaction equation
[C:1]1([CH:7](O)[CH2:8][NH:9][C:10]([NH:18][C:19]#[N:20])=[N:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[C:10](=[N:18][C:19]#[N:20])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178512297HCID 178512297, compound

Product 1

HCID 178512069[5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethane-nitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2-phenyl-2-hydroxyethyl)-N′-cyano-N″-4-pyridylguanidine (1.0 g, 3.56 mmol) and triphenylphosphine (1.86 g, 7.12 mmol) in THF (30 mL) at 0° C. was added diisopropyl azodicarboxylate (3.8 mL, 7.12 mmol) dissolved in 15 mL (THF) by syringe pump over 30 min. The resulting mixture was kept stirring and warmed to room temperature for 70 h. The product was precipitated from ether to form the white solid. The solid thus obtained was washed sequentially with ether, methanol and acetone to give the product (i.e., Compound 14) as a white solid (0.67 g, 72%).

Workup

  1. customThe product was precipitated from ether
  2. customto form the white solid
  3. customThe solid thus obtained
  4. washwas washed sequentially with ether, methanol and acetone

Sources & evidence

ORD record
ord-4f4dd6bbc8f94a92bd02e1e95cb68ecf
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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