Water → HCID 86210898, compound

HRID 1353027Notes

Reaction equation

HRID 1353027 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O)=[N+:17]=[N-:18].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([O:1][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:16]=[N+:17]=[N-:18])[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 21101477HCID 21101477, compound

Product 1

HCID 86210898HCID 86210898, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5-(6-Azidohexoxy)isophthalic Acid Dimethyl Ester was prepared as follows: A mixture of dimethyl 5-hydroxyisophthalate 4 (1.05 g, 5 mmol), 6-azido-1-(p-toluenesulfonyloxy)hexane (1.57 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in DMF (15 mL) was stirred for 17 h at 80° C. After cooling down, H2O (150 mL) was added and the mixture was extracted with EtOAc, washed with water, dried (MgSO4), and the solvent was evaporated off. The pure title compound was obtained as a colorless oil (1.51 g, 90%) after column chromatography (SiO2: CH2Cl2).

Workup

  1. temperatureAfter cooling down
  2. extractionthe mixture was extracted with EtOAc
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-2448631c931140bda76e6b696f24f348
Source dataset
uspto-grants-2007_05
Patent number
US07220818B2

Reaction notes

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