4-(Chlorosulfonyl)-2-hydroxybenzoic acid → HCID 18786172, compound

HRID 1107937Notes

Reaction equation

HRID 1107937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:11]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([OH:16])=[CH:14][CH:15]=1)=[O:9].Cl[S:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([OH:36])[CH:28]=1)(=[O:26])=[O:25]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][S:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([OH:36])[CH:28]=2)(=[O:26])=[O:25])=[C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 18786178HCID 18786178, compound

Product 1

HCID 18786172HCID 18786172, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure in Example 4 using (2-chloro-phenyl)-(6-hydroxy-biphenyl-3-yl)-methanone (0.300 g, 0.972 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.436 g, 1.84 mmol) in THF. Purification by preparative HPLC (C18, eluting with CH3CN/H2O containing 0.1 % TFA), followed by crystallization from EtOAc/hexane gave 0.34 g (69%) of the title compound as a tan solid, mp 101-102° C. 1H NMR (DMSO-d6) δ 6.82 (d, 1H), 6.85 (dd, 1H), 7.14-7.16 (m, 2H), 7.27-7.33 (m, 3H), 7.52-7.54 (m, 1H), 7.58-7.65 (m, 5H), 7.71 (d, 1H), 7.81 (dd, 1H). IR (KBr) 3400, 3050, 1675, 1390 and 1190 cm-1. mass spectrum (EI) m/z 508 (M +). Anal. Calcd. for C26H17ClO7S 0.5H2O: C,60.29; H,3.50; N,0.00. Found: C,60.35; H,3.68; N,0.14.

Workup

  1. customThe title compound was prepared
  2. customPurification
  3. washby preparative HPLC (C18, eluting with CH3CN/H2O containing 0.1 % TFA)
  4. customfollowed by crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-83406c49908845dd80c43ac956c03cf7
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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