Triethylamine → HCID 19081776, compound

HRID 963422Notes

Reaction equation

HRID 963422 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C.[I:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[NH:14][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([I:22])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743783-Iodobenzoyl chlorideHCID 11106041Bis(2-pyridyl)methylamine

Product 1

HCID 19081776HCID 19081776, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g of C,C-dipyridin-2-yl-methylamine are suspended in 50 ml of methylene chloride and 1.15 ml of triethylamine and treated dropwise at 0° with a solution of 3-iodo-benzoyl chloride. After 1 hr. at 0° the reddish suspension is concentrated, the residue is poured into water and extracted three times with methylene chloride. Chromatography on silica gel with methylene chloride/methanol 9:1 yields 1.31 g of brownish N-(di-pyridin-2-yl-methyl)-3-iodo-benzamide. Yield: 39%. Mass spectrum: peaks inter alia at m/e: 415 (M+, 8%), 320 (44%), 231 (36%), 184 (100%).

Workup

  1. concentrationat 0° the reddish suspension is concentrated
  2. additionthe residue is poured into water
  3. extractionextracted three times with methylene chloride

Sources & evidence

ORD record
ord-c05c946c3a684f4896cc682b140c9394
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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