Methyl Salicylate → HCID 9892423, compound

HRID 2186635Notes

Reaction equation

HRID 2186635 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:12]([NH2:21])[CH2:13][N:14]([CH2:18][CH2:19][NH2:20])[CH2:15][CH2:16][NH2:17].[K+].[Br-]>>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([CH:12]([NH2:21])[CH2:13][N:14]([CH2:18][CH:19]([NH2:20])[C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH2:15][CH:16]([NH2:17])[C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])=[O:10]

Participants

4

Reactant 3

HCID 4133Methyl SalicylateHCID 77731Tris(2-aminoethyl)amineHCID 253877Potassium Bromide

Product 1

HCID 9892423HCID 9892423, compoundYield 47%

Conditions

Temperature
100 °C

Procedure

Methyl salicylate (78 mmol) was mixed with distilled TREN (17 mmol). The mixture was sealed and heated to 100° C. overnight. The thick resulting oil was purified on a silica column eluted with 0-4% MeOH in CH2Cl2, resulting in a white powder after removal of solvent. Overnight drying in vacuo gave a colorless glass. Yield: 47%. IR (KBr) 1543, 1590, 1636 cm31 1. 1H NMR(300 MHz, CD3OD, 25 C) 2.78 (t, 3J=6.2 Hz, 6H, CH2), 3.49 (t, 3J=6.2 Hz, 6H, CH2), 6.68 (t, 3J=7.2 Hz, 3H, ArH), 6.80 (d, 3J=7.4 Hz, 3H, ArH), 7.23 (t, 3J=5.8 Hz, 3H, ArH), 7.63 (d, 3J=6.4 Hz, 3H, ArH), 8.44 (t br, 3H, NH). 13C NMR (400 MHz, CD3OD, 25 C) 39.0 (CH2), 54.6 (CH2), 117.1 (Ar), 118.4 (Ar), 120.2 (Ar), 129.0 (Ar), 134.7 (Ar), 160.9 (ArCO), 170.9 (C═O). Anal. Calcd (Found) for C27H30N4O6: C, 64.02 (63.94); H, 5.97 (5.97); N, 11.06 (11.01).

Workup

  1. customThe mixture was sealed
  2. customThe thick resulting oil
  3. customwas purified on a silica column
  4. washeluted with 0-4% MeOH in CH2Cl2
  5. customresulting in a white powder
  6. customafter removal of solvent
  7. customOvernight drying in vacuo
  8. customgave a colorless glass

Sources & evidence

ORD record
ord-3a3d481bb9084112a22e541d32d9c568
Source dataset
uspto-grants-2002_06
Patent number
US06406297B1

Reaction notes

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