4-Nitrobenzenesulfonyl chloride → HCID 22918868, compound

HRID 1377117Notes

Reaction equation

HRID 1377117 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]([OH:36])[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35]>CCOC(C)=O>[CH2:14]([O:36][S:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[O:11])=[O:12])[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 5265552,5,8,11,14,17,20-Heptaoxadocosan-22-ol

Product 1

HCID 22918868HCID 22918868, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6.7 g (60 mmol) of TEA are dropwise added, in 10 min, to a solution of 13.3 g (60 mmol) of 4-nitrobenzenesulfonyl chloride (marketed product) and of 20.4 g (60 mmol) of 3,6,9,12,15,18,21-heptaoxadocosan-1-ol (according to Liebigs Ann. Chem. 1980, 858-862) in 60 mL of AcOEt. After 2 h at the temperature of 20° C., the precipitated TEA hydrochloride is filtered off, washing with 10 mL of AcOEt for three times. The filtrates are collected, washed with 30 mL of H2O, 20 mL of 2N HCl and then with H2O to reach a neutral pH. The organic phase is evaporated to dryness, to give a thick oil which is directly used in the successive step without a further purification. 25 g (47 mmol) of the desired product are obtained.

Workup

  1. filtrationthe precipitated TEA hydrochloride is filtered off
  2. washwashing with 10 mL of AcOEt for three times
  3. customThe filtrates are collected
  4. washwashed with 30 mL of H2O, 20 mL of 2N HCl
  5. customThe organic phase is evaporated to dryness
  6. customto give a thick oil which
  7. customis directly used in the successive step without a further purification

Sources & evidence

ORD record
ord-1a0832aaa0de4e649e1a707b620e7122
Source dataset
uspto-grants-1997_09
Patent number
US05663413

Reaction notes

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