Benzoic acid, 3-(chlorosulfonyl)- → HCID 23296006, compound

HRID 1954303Notes

Reaction equation

HRID 1954303 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH:16]=4)[C:4]=2[C:3]=1[CH3:27])[CH:12]=[CH:11][CH:10]=[CH:9]3.Cl[S:29]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35]([OH:37])=[O:36])(=[O:31])=[O:30]>>[CH:22]1([C:17]2[CH:16]=[C:15]([C:14]3[C:4]4[C:3]([CH3:27])=[C:2]([CH3:1])[S:6][C:5]=4[CH:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)[CH:20]=[CH:19][C:18]=2[O:21][S:29]([C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=2)[C:35]([OH:37])=[O:36])(=[O:31])=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 184307052-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

Product 1

HCID 23296006HCID 23296006, compoundYield 34.4%

Procedure

The title compound was prepared according to the procedure in Example 1, step 9, using 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenol (0.300 g, 0.805 mmol) and commercial 3-chlorosulphonylbenzoic acid (0.600 g, 2.71 mmol). Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil, eluting with 20% EtOAc/hexane followed by trituration with hexane gave 0.154 g (20%) of the title compound as a white solid, mp 120-128° C. 1H NMR (DMSO-d6) δ 1.23-1.36 (m, 2 H), 1.42-1.52 (m, 6 H), 1.55-1.69 (m, 3 H), 2.42 (s, 3 H), 2.96 (quintet, 1 H), 7.23-7.29 (m, 3 H), 7.33 (d, 1 H), 7.39 (ddd, 1 H), 7.47 (ddd, 1 H), 7.90 (t, 1 H), 7.97 (d, 1 H), 8.23 (dd, 1 H), 8.27-8.29 (m, 1 H), 8.37-8.39 (dt, 1 H), 8.50 (s, 1 H), 13.6-13.9 (br s, 1 H). IR (KBr) 3400, 2950, 1700, 1380 and 1190 cm-1. mass spectrum (-ESI) m/z 555 (M-H). Anal. Calcd. for C32H28,O5S2.0.65H2O: C, 67.62; H, 5.20; N, 0.00. Found: C, 67.60; H, 4.90; N, 0.09.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4 /MeOH treated Biotage KP-Sil
  3. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-9d1d24aa8669475e92c80578a01fa204
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

Loading…