Ethanol → HCID 9938136, compound

HRID 1107933Notes

Reaction equation

HRID 1107933 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:12]([O:21][S:22]([C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[C:27]([OH:34])[CH:26]=2)(=[O:24])=[O:23])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:41](N(CCCC)CCCC)[CH2:42]CC.C(O)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl>[CH2:41]([O:30][C:29](=[O:31])[C:28]1[CH:32]=[CH:33][C:25]([S:22]([O:21][C:12]2[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:14][C:9]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][C:11]=2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:23])=[O:24])=[CH:26][C:27]=1[OH:34])[CH3:42]

Participants

6

Reactant 4

HCID 702EthanolHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 9829001HCID 9829001, compound

Product 1

HCID 9938136HCID 9938136, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution containing 4-(5'-benzoyl-[1,1';3',1"]terphenyl-2'-yloxysulfonyl)-2-hydroxy-benzoic acid (0.106 g, 0.192 mmol), tributylamine (0.110 mL, 0.462 mmol), ethanol (0.0677 mL, 1.15 mmol) and 2-chloro-1-methyl pyridinium iodide (0.0607 g, 0.231 mmol) in CH2Cl2 (2 mL) was refluxed for 18 h. The reaction was cooled to ambient temperature, quenched with 1N HCl (20 mL) and extracted with EtOAc. The organic extracts were successively washed with 1N HCl (3×), with brine (3×), dried (MgSO4) and concentrated. Purification on Biotage KP-Sil eluting with 20% acetone/hexane gave 0.039g (35%) of the title compound as a white solid, mp 75-85° C. 1H NMR (DMSO-d6) δ 1.36 (t, 3H), 4.38 (q, 2H), 6.67 (d, 1H), 6.73 (dd, 1H), 7.30-7.36 (m, 6H), 7.45-7.52 (m, 5H), 7.57-7.61 (m, 2H), 7.68-7.71 (m, 3H), 7.84 (d, 2H), 10.60 (s, 1H). mass spectrum (El) m/z 578 (M+). Anal. Calcd. for C34H26O7S 0.5H2O: C,69.49; H,4.63; N,0.00. Found: C,69.38; H,4.76; N,0.10.

Workup

  1. temperaturewas refluxed for 18 h
  2. customquenched with 1N HCl (20 mL)
  3. extractionextracted with EtOAc
  4. washThe organic extracts were successively washed with 1N HCl (3×), with brine (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification on Biotage KP-Sil
  8. washeluting with 20% acetone/hexane

Sources & evidence

ORD record
ord-65913374eedd4b55be4ae8ca93c1dbb6
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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