4-Aminobenzoic Acid → HCID 53702451, compound

HRID 1796891Notes

Reaction equation

HRID 1796891 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:24])([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22]Br)=[O:13].[Cl-].[Cs+]>>[CH3:11][S:12](=[S:24])([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][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

4

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 24293Cesium ChlorideHCID 86602578HCID 86602578, compound

Product 1

HCID 53702451HCID 53702451, compoundYield 70.6%

Procedure

In a manner analogous to that above, the reaction of p-aminobenzoic acid (473 mg; 4.90 mmol), 1-(8-bromo-3,6-dioxaoctyl) methanethiosulfonate (1.04 g, 3.39 mmol) and CsCl (1.17 g, 3.6 mmol) yielded 10-(4-aminophenyl)-10-oxo-3,6,9-trioxadecyl methanethiosulfonate (870 mg). 1H NMR (500 MHz, (CD3)2SO) δ 7.62 (d J=8.6 Hz, 2H), 6,55 (d, J=8.6 Hz, 2H), 5.94 (s, 2H), 4.25 (t, J=4.8 Hz, 2H), 3.72-3.67 (m, 4H), 3.58 (s, br., 4H). 3.51 (s, 3H), 3.35 (t, J=5.9 Hz, 2H).

Sources & evidence

ORD record
ord-a2a2a5f0dd954541a0bf4527580c40f7
Source dataset
uspto-grants-2006_04
Patent number
US07033765B1

Reaction notes

Loading…