4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenoxysulfonyl}-2-hydroxy-benzoic Acid

HRID 1841330Notes

Reaction equation

HRID 1841330 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].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]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH2:10][NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][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])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 234456414-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenol

Product 1

HCID 101414894-{4-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenoxysulfonyl}-2-hydroxy-benzoic AcidYield 85%

Procedure

The title compound was prepared according to the procedure in Example 4 using 4-[(2-butyl-benzofuran-3-ylmethyl)-amino]-phenol (0.500 g, 1.69 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.401 g, 1.69 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with 25% EtOAc/hexane gave 0.571 g (85%) of the title compound as a dark yellow solid, mp 75-77° C. 1H NMR (DMSO-d6) δ0.86 (t, 3 H), 1.31 (sextet, 2 H), 1.60 (quintet, 2 H), 2.80 (t, 2 H), 4.23 (s, 2 H), 6.54 (b, 2 H), 6.72 (d, 2 H), 7.14-7.22 (m, 2 H), 7.26-7.30 (m, 2 H), 7.45 (dd, 1 H), 7.58 (dd, 1 H), 7.95 (d, 1 H). IR (KBr) 3400, 2950, 1600, 1510 and 1380 cm−1. mass spectrum (−ESI) m/z 494 (M−H).

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-752ec66fc0414234953f7d6a62c60a03
Source dataset
uspto-grants-2004_01
Patent number
US06683107B2

Reaction notes

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