Pyridine → HCID 19800414, compound

HRID 2073375Notes

Reaction equation

HRID 2073375 reaction equation
C[O:2][CH2:3][CH:4]([N:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34])[CH2:9][CH2:10][N:11]([CH:20]([C:24]([OH:26])=[O:25])[CH2:21][O:22]C)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[C:5]([OH:7])=[O:6].C[Si](I)(C)C.N1C=CC=CC=1>C(Cl)(Cl)Cl>[OH:22][CH2:21][CH:20]([N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[CH2:10][CH2:9][N:8]([CH:4]([C:5]([OH:7])=[O:6])[CH2:3][OH:2])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34])[C:24]([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85247Trimethylsilyl iodideHCID 19800409HCID 19800409, compound

Product 1

HCID 19800414HCID 19800414, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4.7 g N,N'-bis-(2-methoxy-1-carboxy-1-ethyl)-N,N'-bis-(2-hydroxy-phenylmethyl)-ethylenediamine (Example 17), 16 g trimethyl silyl iodide (0.08 mol), 6.32 g pyridine (0.08 mol) in 10 ml of chloroform is stirred at room temperature overnight, under nitrogen. The reaction mixture is filtered and the solvent evaporated in vacuo. The residue is poured in water giving a solid that after purification by chromatography furnishes N,N'-bis-(2-hydroxy-1-carboxy-1-ethyl)-N,N'-bis-(2-hydroxy-phenylmethyl)-ethylene diamine.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent evaporated in vacuo
  3. additionThe residue is poured in water giving a solid that
  4. customafter purification by chromatography

Sources & evidence

ORD record
ord-335f990d3e6a46b9ad48092d0cb6f7bd
Source dataset
uspto-grants-1990_04
Patent number
US04916246

Reaction notes

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