Valeronitrile → HCID 178441990, compound

HRID 1975276Notes

Reaction equation

HRID 1975276 reaction equation
[C:1](#[N:6])[CH2:2][CH2:3][CH2:4][CH3:5].C([Sn](=O)CCCC)CCC.C[Si]([N:21]=[N+:22]=[N-:23])(C)C>C1(C)C=CC=CC=1>[CH2:2]([C:1]1[NH:23][N:22]=[N:21][N:6]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8061ValeronitrileHCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane

Product 1

HCID 178441990HCID 178441990, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure described in Example 21, valeronitrile (845 mg, 10.16 mmol) was reacted with dibutyltin oxide (254 mg, 1.02 mmol) and trimethylsilyl azide (2.70 ml, 19.8 mmol) in toluene (20 mL) to give 1.088 g (85%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ0.95 (t, J=7 Hz, 3H), 1.43 (sextet, J=7 Hz, 2H), 1.87 (pentet, J=7 Hz, 2H), 3.12 (t, J=7 Hz, 2H). 13C NMR (CDCl3, 75 MHz) 13.42, 22.04, 23.08, 29.62, 156.94. IR (CDCl3) 2900, 1555 cm-1. MS (DCl/NH3) m/e 127 (M+H)+, 144 (M+H+NH3)+. Anal calcd for C5H10N4 : C, 47.60; H, 7.99; N, 44.41. Found: C, 47.14; H, 7.99; N, 43.75.

Sources & evidence

ORD record
ord-05663169e5bf4eb9bd1b92dd2bf6046f
Source dataset
uspto-grants-1994_02
Patent number
US05284954

Reaction notes

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