Ethanol → Deferasirox Ethyl Ester

HRID 991736Notes

Reaction equation

HRID 991736 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:10]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[N:9]=1.S(=O)(=O)(O)O.[CH2:34](O)[CH3:35]>>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:10]([C:20]2[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:34][CH3:35])=[O:25])=[CH:27][CH:28]=2)[N:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 214348Deferasirox

Product 1

HCID 135817477Deferasirox Ethyl Ester

Procedure

10 g of 4-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]benzoic acid (Example 5) and 0.5 ml of sulfuric acid are boiled under reflux for 20 h in 200 ml of ethanol. The crystals precipitating on cooling are crystallized from isopropanol/water. After drying, ethyl 4-[3,5-bis(2-hydroxy-phenyl)-[1,2,4]triazol-1-yl]benzoate is obtained as colorless crystals of m.p. 148-149° C.

Workup

  1. customThe crystals precipitating
  2. temperatureon cooling
  3. customare crystallized from isopropanol/water
  4. customAfter drying

Sources & evidence

ORD record
ord-017bc7d6e8db4d688be772e063d27793
Source dataset
uspto-grants-2002_10
Patent number
US06465504B1

Reaction notes

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