Triethylamine → HCID 19605504, compound

HRID 1603630Notes

Reaction equation

HRID 1603630 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=O)[CH:5]=[C:4]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]#[N:10])[CH:5]=[C:4]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 19605498HCID 19605498, compound

Product 1

HCID 19605504HCID 19605504, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 22018518Dioxane tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.76 g (0.0044 mol) of 6-bromo-4-(4-nitrobenzenesulphonyl)-pyridine-2-carboxamide were suspended in 11 ml of dioxane/THF 1:1, treated with 1.34 ml (0.0096 mol) of triethylamine and cooled to 0° C. 0.69 ml (0.00496 mol) of trifluoroacetic anhydride was slowly added dropwise to this suspension and the mixture was left to warm to room temperature and stirred for 1 hr. The reaction mixture was partitioned in ethyl acetate and water and the organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:4. There were obtained 1.40 g (87%) of 6-bromo-4-(4-nitrobenzenesulphonyl)-pyridine-2-carbonitrile as yellowish crystals; m.p.: 158-160° C.

Workup

  1. waitthe mixture was left
  2. temperatureto warm to room temperature
  3. customThe reaction mixture was partitioned in ethyl acetate
  4. washwater and the organic phase was washed with water and sat. sodium chloride solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:4

Sources & evidence

ORD record
ord-d879a82de0234bacb21453b8f56388f0
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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