Triethylamine → HCID 178457340, compound

HRID 1250980Notes

Reaction equation

HRID 1250980 reaction equation
[N+:1]([C:4]1[N:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[P:17]([O:25][CH2:26][CH2:27][C:28]#[N:29])[N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20]>C1COCC1>[C:28]([CH2:27][CH2:26][O:25][P:17]([N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:20])[CH3:21])[C:7]1[NH:6][N:5]=[C:4]([N+:1]([O-:3])=[O:2])[N:8]=1)#[N:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramiditeHCID 178526901HCID 178526901, compound

Product 1

HCID 178457340HCID 178457340, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-nitro-1,2,4-triazole (9.64 g, 84.50 mmol) and triethylamine (14.0 mL, 10.26 g, 101.4 mmol) in THF (200 mL) was added dropwise chloro-2-cyanoethoxy-N,N-diisopropylaminophosphine (20.0 g, 84.50 mmol) at room temperature. The mixture was stirred overnight at room temperature. The reaction mixture was filtered to remove the resulting salt, and the solvent was removed under reduced pressure to give the crude product as a pale brown oil (24.9 g, 95%). After standing at room temperature, the oil becomes a pale yellow wax-like solid. 1H NMR (CDCl3 δ 8.39 (s, 1H), 4.09 (m, 2H), 3.51 (m, 2H), 2.81 (m, 2H), 1.19 (d, J=6.0 Hz, 6H), 1.07 (d, J=9.0 Hz, 6H). 31P NMR (CDCl3) δ 133.9.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the resulting salt
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-13337c9efd234c05a505f2fb47b47483
Source dataset
uspto-grants-2002_01
Patent number
US06340749B1

Reaction notes

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