Hydrochloric Acid → 2-Chlorobenzenesulfonic acid 3-[(3-amidinophenyl)methoxy]phenyl ester hydrochloride

HRID 368546Notes

Reaction equation

HRID 368546 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([O:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.C(=O)([O-])[O-].[NH4+:33].[NH4+]>C(Cl)Cl.C(O)C>[ClH:27].[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([O:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1)(=[NH:33])[NH2:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 538328372-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester

Product 1

HCID 867552152-Chlorobenzenesulfonic acid 3-[(3-amidinophenyl)methoxy]phenyl ester hydrochlorideYield 150%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester (280 mg, 0.7 mmol), as prepared in the preceding step, in methylene chloride (10 mL) was added 37% HCl in ethanol (15 mL) at 0° C. The mixture was stirred at room temperature for 2 days. The solvent was evaporated and the residue was co-evaporated with methylene chloride several times. The residue was then dissolved in ethanol (10 mL) and ammonium carbonate (300 mg, 3.0 mmol) was added at 0° C. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride (150 mL), washed with 10% K2CO3 (2×50 mL), and dried over K2CO3. The solvent was removed in vacuo, HCl in methanol (30 mL) was added, and then concentrated in vacuo. The residue was purified by flash chromatography (10% methanol in methylene chloride) to give the title compound as a white foam (238 mg, 75%). 1H-NMR (300 MHz, DMSO-d6) δ 5.15 (s, 2 H), 6.67 (d, 1 H, J=4.0 Hz), 6.81 (s, 1 H), 7.03 (d, 1H, J=4.0 Hz), 7.32 (t, 1 H, J=8.3 Hz), 7.58 (t, 1 H, J=7.5 Hz), 7.65 (t, 1 H, J=7.7 Hz), 7.75-7.94 (m, 6 H), 9.27 (br s, 2 H), and 9.45 (br s, 2 H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H17N2ClO4S: 417.1 (M+H), 439.0 (M+Na). Found: 417.4, 439.1.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was then dissolved in ethanol (10 mL)
  3. stirringThe mixture was stirred at room temperature overnight
  4. washwashed with 10% K2CO3 (2×50 mL)
  5. dry with materialdried over K2CO3
  6. customThe solvent was removed in vacuo, HCl in methanol (30 mL)
  7. additionwas added
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-9c9d836f69114dc6b74328bf0b05f85f
Source dataset
uspto-grants-2000_10
Patent number
US06133315

Reaction notes

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