Ethylene glycol ditosylate → HCID 86651378, compound

HRID 1879569Notes

Reaction equation

HRID 1879569 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([NH:15][CH:16]=[O:17])=[CH:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:28][CH2:29][CH2:30]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:28][CH2:29][CH2:30][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11](=[CH:10][C:9]([NH:15][CH:16]=[O:17])=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH:14]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 228289Ethylene glycol ditosylateHCID 58160250N-(7-hydroxy-9H-carbazol-2-yl)formamide

Product 1

HCID 86651378HCID 86651378, compound

Procedure

Compound 2-(7-formamido-9H-carbazol-2-yloxy)ethyl 4-methylbenzenesulfonate (AD-CB-012P-WZ02039) was prepared using the same procedure for the preparation of AD-CB-012S-WZ01185) from N-(7-hydroxy-9H-carbazol-2-yl)formamide (100 mg) and ethane-1,2-diyl bis(4-methylbenzenesulfonate) (325 mg). (white solid, 22 mg, 12%). For the major rotomer: 1H NMR (400 MHz, acetone-d6) δ 10.19 (s, 1H), 9.31 (s, 1H), 8.38 (d, J=1.6 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 7.90-7.81 (m, 4H), 7.45 (d, J=8.4 Hz, 2H), 7.19 (dd, J=8.4, 2.0 Hz, 1H), 6.95 (d, J=2.0 Hz, 1H), 6.69 (dd, J=8.4, 2.0 Hz, 1H), 4.43-4.41 (m, 2H), 4.29-4.27 (m, 2H); MS (ESI) m/z 425 (M+H+).

Sources & evidence

ORD record
ord-d76eef448be84b9592fb2148c23bba1a
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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