Benzenesulfonyl chloride → 24396-72-3

HRID 232507Notes

Reaction equation

HRID 232507 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH2:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:11]([NH:23][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 13583Dodecylamine

Product 1

HCID 365849924396-72-3Yield 82.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Benzenesulfonyl chloride (353 g, 2 mol) was added dropwise to a toluene (2000 mL) solution of dodecylamine (371 g, 2 mol) and triethylamine (203 g, 2 mol) with ice bath cooling. During the one hour addition period, the temperature increased to about 40° C. After filtration of the triethylamine hydrochloride, the toluene solution was washed with dilute HCl, dilute NaOH and water. After drying over magnesium sulfate, the toluene was removed in vacuo and the precipitate slurried in hexane and filtered to give 539 g of product. Melting point 57-60° C. Calculated for C18H32NO2S 326, found 326. 1H NMR (CDCl3) δ0.88 (t, 3, CH3), 1.24 (d, 18, CH2), 1.45 (s, 2, CH2), 4.66 (sb, 1, NH), 7.49-7.84 (m, 5, arom.).

Workup

  1. temperaturecooling
  2. additionDuring the one hour addition period
  3. filtrationAfter filtration of the triethylamine hydrochloride
  4. washthe toluene solution was washed with dilute HCl, dilute NaOH and water
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe toluene was removed in vacuo
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d99ec31f32354b4da913f62f30d4e598
Source dataset
uspto-grants-1997_01
Patent number
US05591503

Reaction notes

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