Water → HCID 18436661, compound

HRID 456407Notes

Reaction equation

HRID 456407 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].N1C=CC=CC=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C(Cl)Cl>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[S:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8113Diethanolamine

Product 1

HCID 18436661HCID 18436661, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethanolamine (8.40 g, 80 mmol, 1.50 equiv) was dissolved in CH2Cl2 (30 mL) and pyridine (5.1 mL, 63.6 mmol, 1.2 equiv). A solution of 4-methoxybenzenesulfonyl chloride (10.9 g, 53 mmol, 1.0 equiv) n CH2Cl2 (30 mL) was added quickly and the resulting mixture was stirred at rt overnight, then poured into H2O and extracted with EtOAc. The organic layers were washed with 1M HCl and brine, dried (MgSO4), filtered, and the filtrate was concentrated to give an oil which was purified by column chromatography (95/5 CH2Cl2/MeOH) to give 12 g (83%) of the sulfonamide as an oil which crystallized on standing: 1H NMR (500 MHz) 7.75 (d, J=8.8, 2H, HAr); 6.99 (d, J=8.8, 2H, HAr); 3.87 (a, 3H, H3CO); 3.86 (t, J=4.9, 4 H, H2C(1′); 3.42 (br s, 2H, OH); 3.26 (t, J=4.9, 4H, H2C(2′)). 13C NMR (100 MHz) 163.05; 129.85; 129.37; 114.37; 62.25; 55.61; 52.90.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with 1M HCl and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give an oil which
  7. customwas purified by column chromatography (95/5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-036285d1f6144ca68094627ddeca28e2
Source dataset
uspto-grants-2007_03
Patent number
US07186709B2

Reaction notes

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