Pyridine → HCID 19800414, compound

HRID 1111485Notes

Reaction equation

HRID 1111485 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-10b99ba033bf497387f4a71e1589b0d2
Source dataset
uspto-grants-1990_12
Patent number
US04980502

Reaction notes

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