4-(Chlorosulfonyl)-2-hydroxybenzoic acid → HCID 9874697, compound

HRID 1107935Notes

Reaction equation

HRID 1107935 reaction equation
[OH:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[I:19].Cl[S:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[C:26]([OH:33])[CH:25]=1)(=[O:23])=[O:22]>C1COCC1>[I:19][C:3]1[CH:4]=[C:5]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:6]=[C:7]([I:8])[C:2]=1[O:1][S:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[C:26]([OH:33])[CH:25]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 23450825HCID 23450825, compound

Product 1

HCID 9874697HCID 9874697, compoundYield 16%

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)-(4-methoxy-phenyl)-methanone (0.202 g, 0.421 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.398 g, 1.68 mmol) in THF (5 mL). Purification by preparative HPLC (C18, eluting with 70% CH3CN/H2O containing 0.1% TFA) gave 0.045 g (16%) of the title compound as a white solid, mp 214-215° C. 1H NMR (DMSO-d6) δ 3.86 (s, 3H), 7.11 (d, 2H), 7.44-7.48 (m, 2H), 7.73 (d, 2 H), 8.04-8.07 (m, 3H). IR (KBr) 3400, 3050, 1690, 1600, 1260 and 1175 cm-1. mass spectrum (-ESI) m/z 679 (M-H). Anal. Calcd. for C21H14I2O8S: C,37.08; H,2.07; N,0.00. Found: C,37.43; H,2.24; N,0.00.

Workup

  1. customThe title compound was prepared
  2. customPurification
  3. washby preparative HPLC (C18, eluting with 70% CH3CN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-fe54d3cc8a6c427ba16ce87fb5754ff4
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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