Ethanolamine → HCID 43502079, compound

HRID 1914702Notes

Reaction equation

HRID 1914702 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.C(N(CC)CC)C.[CH2:23]([CH2:25][NH2:26])[OH:24].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[OH:24][CH2:23][CH2:25][NH:26][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:13]([O-:15])=[O:14])(=[O:11])=[O:10]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 874524-Methoxy-2-nitrobenzenesulphonyl chloride

Product 1

HCID 43502079HCID 43502079, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-2-nitrobenzenesulfonyl chloride (3.1 g; 12.3 mmol; 1 eq) is dissolved in DCM (60 mL) in the presence of triethylamine (1.7 mL; 12.3 mmol; 1 eq) at 0° C. Ethanolamine (0.6 mL; 13.6 mmol; 1.1 eq) is then added and the reaction mixture is stirred at room temperature for 16 h. Water is added to the reaction mixture then aqueous Na2CO3. The organic phase is dried over MgSO4 and the solvent is evaporated under reduced pressure to give 2.9 g (85%) of the title compound as an orange oil, 1H NMR (DMSO-d6) δ 7.92 (d, J=3.2 Hz, 1H), 7.85-7.78 (m, 1H), 7.56 (d, J=2.5 Hz, 1H), 7.37 (dd, J=8.9, 2.6 Hz, 1H), 4.79-4.71 (m, 1H), 3.90 (s, 3H), 3.42-3.46 (m, 2H), 2.92-2.87 (m, 2H). HPLC (max plot) 52.3%; Rt 220 min. UPLCIMS: (ES+) 277.2, (ES−) 275.2.

Workup

  1. dry with materialThe organic phase is dried over MgSO4
  2. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-0a7fb119a7d64ca4a0aa775d89c8cbac
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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