Triethylamine → HCID 59402852, compound

HRID 415582Notes

Reaction equation

HRID 415582 reaction equation
[C:1]1(C)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH2:12](N(CC)CC)C.[OH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:31]=[C:32]([C:36]([NH2:38])=[O:37])[CH:33]=[CH:34][CH:35]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:12][C:5]1[CH:6]=[CH:1][C:2]([S:7]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([NH2:38])=[O:37])[CH:31]=2)(=[O:8])=[O:9])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59402748HCID 59402748, compound

Product 1

HCID 59402852HCID 59402852, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Toluenesulfonyl chloride (410 mg, 2.15 mmol, 1.5 equiv.) and triethylamine (0.40 ml, 2.88 mmol, 2 equiv.) were added to a solution of 3-[(9-hydroxynonyl)oxy]benzenecarboxamide (400 mg, 1.43 mmol, 1 equiv.) in CH2Cl2 (4 ml) and the reaction mixture was stirred at r.t. for 6 days. Saturated NaHCO3 solution (40 ml) was added and the mixture was extracted with CH2Cl2 (3×30 ml). The combined organic extracts were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with CH3OH/CH2Cl2 (2%), to give the desired compound as white solid (428 mg, 69%), mp 78-80° C. HPLC-MS (method 1): m/z 434 [M+H]+, Rt=4.90 min.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×30 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica eluting with CH3OH/CH2Cl2 (2%)

Sources & evidence

ORD record
ord-b12ac8c315aa4f67a2ab31e5b7bd1a7f
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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