4-Aminobenzoic Acid → HCID 22174364, compound

HRID 1796892Notes

Reaction equation

HRID 1796892 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:21])([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19]Br)=[O:13].[Cl-].[Cs+]>>[CH3:11][S:12](=[S:21])([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][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 86602579HCID 86602579, compound

Product 1

HCID 22174364HCID 22174364, compoundYield 14.7%

Procedure

In a manner analogous to that above, the reaction of p-aminobenzoic acid (671 mg; 4.90 mmol), 1-(5-bromo-3-oxapentyl) methanethiosulfonate (1.29 g, 4.9 mmol) and CsCl (1.63 g, 5 mmol) yielded 7-(4-aminophenyl)-7-oxo-3,6-dioxaheptyl methanethiosulfonate (230 mg). 1H NMR (500 MHz, (CD3)2SO) δ 7.62 (d, J=8.7 Hz, 2H), 6.55 (d, J=8.7 Hz, 2H), 5.95 (s, br., 2H), 4.27 (t, J=4.7 Hz, 2H), 3.77 (t, J=6.0 Hz, 2H), 3.73 (t, J=4.7 Hz, 2H), 3.50 (s, 3H), 3.39 (t, J=6.0 Hz, 2H).

Sources & evidence

ORD record
ord-545fd410c1264833b97ac17b7dafee93
Source dataset
uspto-grants-2006_04
Patent number
US07033765B1

Reaction notes

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