Triethylamine → HCID 11439535, compound

HRID 2400263Notes

Reaction equation

HRID 2400263 reaction equation
[F:1][C:2]1[C:7]2=[N:8][Se:9][N:10]=[C:6]2[C:5]([S:11](Cl)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[CH2:15]([N:17]([CH2:21]C)[CH2:18][CH2:19][NH2:20])C.C(N(CC)CC)C>C(#N)C>[F:1][C:2]1[C:7]2=[N:8][Se:9][N:10]=[C:6]2[C:5]([S:11]([NH:20][CH2:19][CH2:18][N:17]([CH3:21])[CH3:15])(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60993N,N-DiethylethylenediamineHCID 86055263HCID 86055263, compound

Product 1

HCID 11439535HCID 11439535, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-fluoro-2,1,3-benzoselenadiazole-4-sulfonyl chloride (75 mg) was dissolved in 3 ml of acetonitrile. After the addition of N,N-diethylethylenediamine (22 mg) and triethylamine (351), the mixture was stirred on ice for 30 min. The reaction mixture was evaporated to dryness in vacuo and the residue was dissolved in CH2Cl2 and chromatographed on silica gel using CH2Cl2-CH3OH (93:7) to yield 7-fluoro-N-[2-(dimethylamino)ethyl]-2,1,3-benzoselenadiazole-4-sulfonamide (49 mg, 56%) as red powder. mp: 117-120° C. 1H-NMR δH8.09 (1H, d, J=7.5 Hz), 7.24 (1H, d, J=7.5 Hz), 2.93 (2H, t, J=6.7 Hz), 2.27 (2H, t, J=6.7 Hz), 1.98 (6H, s) in CD3OD; ESI-MSm/z 353 [(M+H)+]

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-0c926c8d6ef64ecdbf28f79a6b1d6755
Source dataset
uspto-grants-2014_08
Patent number
US08796037B2

Reaction notes

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