Triphenylphosphine → 5-Aminomethyl-2-cyanothiophene

HRID 1263424Notes

Reaction equation

HRID 1263424 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:22]1[S:23][C:24]([CH2:27][N:28]=[N+]=[N-])=[CH:25][CH:26]=1)#[N:21]>C1COCC1.O>[C:20]([C:22]1[S:23][C:24]([CH2:27][NH2:28])=[CH:25][CH:26]=1)#[N:21]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 22229400HCID 22229400, compound2×

Product 1

HCID 98340895-Aminomethyl-2-cyanothiopheneYield 166.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (Aldrich, 5.7 g) was added to a solution of 2-cyano-5-(azidomethyl)thiophene (compound 24, 2.5 g, 10 mmol) in THF (Aldrich, 40 mL) and water (10 mL) at 0° C. The solution was allowed to warm to room temperature and stirred at ambient temperature for 10 hours. RP-HPLC purification gave the title compound (2.3 g, 94%). MS (electrospray) 139 (M+1); 1HNMR (CDCl3) δ4.01 (s, 2H), 4.75 (br s, 2H, NH2), 6.82 (d, 1H, J=3.5 Hz), 7.08 (d, 1H, J=3.5 Hz).

Workup

  1. customRP-HPLC purification

Sources & evidence

ORD record
ord-5f7c3c1893dd4e6b84d34c5e332234c3
Source dataset
uspto-grants-2003_04
Patent number
US06541467B1

Reaction notes

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