4-Aminobenzoic Acid → HCID 69585939, compound

HRID 1796890Notes

Reaction equation

HRID 1796890 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][S:12](=[S:30])([O:14][CH:15](Br)[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH3:28])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:11][S:12](=[S:30])([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:7][C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[CH:3][CH:4]=1)=[O:8])=[O:13]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 10796Cesium carbonateHCID 86759986HCID 86759986, compound

Product 1

HCID 69585939HCID 69585939, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-aminobenzoic acid (0.145 g, 1.06 mmol) and 1-bromo-3,6,9,12-tetraoxatetradecyl methanethiosulfonate (0.42 g, 1.06 mmol) were dissolved in dry DMF (30 mL). Cesium carbonate (0.385 mg, 1.1 mmol) was added and the mixture was stirred at room temperature for 3 days. The solvent was evaporated. The residue was pied by column chromatography on SiO2. Elution was with dichloromethane/methanol (100:3) and after evaporation, 16-(4-aminophenyl)-16-oxo-3,6,9,12,1 5-pentaoxahexadecyl methanethiosulfonate (0.120 g, 0.27 mmol; 25% yield) remained as a pale yellow oil. 1H NMR (500 MHz, (CD3)2SO) δ 7.62 (d, J=8.7 Hz, 2H), 6.55 (d, J=8.7 Hz, 2H), 5.94 (s, br., 2H), 4.25 (t, J=4.8 Hz, 2H), 3.70-3.67 (m, 4H), 3.57-3.55 (m, 2H), 3.54-3.47 (m, 13H), 3.36 (t, J=5.9 Hz, 2H).

Workup

  1. customThe solvent was evaporated
  2. washElution

Sources & evidence

ORD record
ord-8bbf8c31cce74599a030cbbf4b3035eb
Source dataset
uspto-grants-2006_04
Patent number
US07033765B1

Reaction notes

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