Triethylamine → HCID 21709975, compound

HRID 650893Notes

Reaction equation

HRID 650893 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[C:13]1(C)C=CC=C[C:14]=1[ClH](C1C=CC=CC=1C)(C1C=CC=CC=1C)C(Cl)=O.C(N(CC)CC)C>C(#N)C.[Pd]>[CH:13]([C:2]1[N:3]=[N+:4]([O-:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)=[CH2:14]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 2507133-chloro-1,2,4-benzotriazine 1-oxide

Product 1

HCID 21709975HCID 21709975, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

3-chloro-1,2,4-benzotriazine 1-oxide was treated with a slight excess of tri-N-butylvinyltin in a mixture of acetonitrile, tritoluyl phosgene and triethylamine, using palladium II catalysis (Pd II acetate) in a sealed tube at 100° C. for 48 hours. Removal of solvent and purification by column chromatography gave 3-vinyl-1,2,4-benzotriazine 1-oxide (33). Reduction with 9-borabicyclo [3.3.1] nonane (9-BBN) followed by oxidation with sodium hydroxide and hydrogen peroxide gave the title compound 3-(1-hydroxyethyl)-1,2,4-benzotriazine 1-oxide (34).

Workup

  1. customat 100° C.
  2. customfor 48 hours
  3. customRemoval of solvent and purification by column chromatography

Sources & evidence

ORD record
ord-5fc17f60509c4a458a9f2651a1f66d45
Source dataset
uspto-grants-2001_08
Patent number
US06277835B1

Reaction notes

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