Ethanolamine → HCID 11266237, compound

HRID 1991193Notes

Reaction equation

HRID 1991193 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12].[CH2:17]([CH2:19][NH2:20])[OH:18]>C(O)C>[OH:18][CH2:17][CH2:19][NH:20][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 11391437HCID 11391437, compound

Product 1

HCID 11266237HCID 11266237, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (170 mg, 0.642 mmol) and ethanolamine (196 mg, 3.21 mmol) in ethanol (6 mL) was heated at reflux for 4 h. The solvent was removed in vacuo, and the residue was purified by column chromatography using heptane/ethyl acetate, 1:1 as an eluent affording 2-[(2-hydroxyethyl)amino]-N,N-dimethyl-3-nitrobenzenesulfonamide, 161 mg (87%). MS (ESI) mm/z 288 [M−H]. 1H NMR (400 MHz, CDCl3) δ ppm 1.92 (t, J=5.6 Hz, 1H), 2.83 (s, 6 H), 3.10-3.06 (m, 2H), 3.84-3.80 (m, 2H), 6.83 (t, J=8.0 Hz, 1H), 6.87 (broad s, 1H), 7.91-7.87 (m, 2H).

Workup

  1. temperatureat reflux for 4 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d77804aab8546b4bbfe1a7954839427
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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