(4-Hydroxy-3,5-diiodo-phenyl)-phenyl-methanone → 4-(4-Benzoyl-2,6-diiodo-phenoxysulfonyl)-2-hydroxy-benzoic acid

HRID 1107938Notes

Reaction equation

HRID 1107938 reaction equation
[OH:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[I:17].Cl[S:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([OH:31])[CH:23]=1)(=[O:21])=[O:20]>C1COCC1>[C:9]([C:5]1[CH:4]=[C:3]([I:17])[C:2]([O:1][S:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([OH:31])[CH:23]=2)(=[O:21])=[O:20])=[C:7]([I:8])[CH:6]=1)(=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 9911585(4-Hydroxy-3,5-diiodo-phenyl)-phenyl-methanoneHCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 99611224-(4-Benzoyl-2,6-diiodo-phenoxysulfonyl)-2-hydroxy-benzoic acidYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure in Example 4 using (4-hydroxy-3,5-diiodo-phenyl)-phenyl-methanone (0.346 g, 0.768 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.928 g, 3.92 mmol) in THF. Purification On Biotage KP-Sil, eluting with 10% MeOH/CHCl3 followed by crystallization from EtOAc/hexane gave 0.15 g (30%) of the title compound as an orange solid, mp 190° C. 1H NMR (DMSO-d6) δ 7.22-7.35 (m, 2H), 7.58 (t, 2H), 7.69-7.75 (m, 3H), 7.95 (d, 1H), 8.10 (s, 2H). IR (KBr) 3400, 3100, 1660, 1280 and 1180 cm-1. mass spectrum (+FAB) m/z 651 (M+H). Anal. Calcd. for C20H12I2O7S 0.5H2O: C,36.44; H,1.99; N,0.00. Found: C,36.50; H,2.16; N,0.09.

Workup

  1. customThe title compound was prepared
  2. customPurification On Biotage KP-Sil
  3. washeluting with 10% MeOH/CHCl3
  4. customfollowed by crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-de9d0107785d4eada40978ab9ef19e2d
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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