Acetone → HCID 22011778, compound

HRID 1532963Notes

Reaction equation

HRID 1532963 reaction equation
[CH2:1]([N:8]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][OH:30])[CH2:9][CH2:10][C:11]12[CH:21]=[CH:20][CH:19]=[CH:18][CH:12]1[C:13]([NH:15][C:16]2=[O:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].CC(C)=O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.ClCCl.C(Cl)(Cl)Cl>[CH2:1]([N:8]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:9][CH2:10][C:11]12[CH:21]=[CH:20][CH:19]=[CH:18][CH:12]1[C:13]([NH:15][C:16]2=[O:17])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22011775HCID 22011775, compound

Product 1

HCID 22011778HCID 22011778, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-[2-(Benzyl-{2-[2-(2-hydroxy-ethoxy)ethoxy]ethyl}amino)ethyl]phthalimide 33 (2.774 g, 6.7 mmol) was dissolved in mixture of pyridine (20 mL) and dichloromethane (100 mL) and cooled in an ice bath. Methanesulfonyl chloride (0.63 mL, 8 mmol) was added and the resulting solution was stirred at 0° C. for 16 h. (The progress of the reaction was followed by TLC using a 1:1 mixture of 40% acetone in hexanes and chloroform as the eluent. The starting material has Rf=0.35, while the product has Rf=0.50.) Saturated aqueous sodium bicarbonate was added, and after 30 min of stirring, the organic phase was washed with 0.5 M hydrochloric acid and again with saturated aqueous sodium bicarbonate. The solution was dried over sodium sulfate and solvent was removed under reduced pressure. The resulting crude oily product 34 (3.152 g, 96%) was used in the next step without further purification. CIMS (M+): 491.

Workup

  1. temperaturecooled in an ice bath
  2. stirringafter 30 min of stirring
  3. washthe organic phase was washed with 0.5 M hydrochloric acid and again with saturated aqueous sodium bicarbonate
  4. dry with materialThe solution was dried over sodium sulfate and solvent
  5. customwas removed under reduced pressure
  6. customThe resulting crude oily product 34 (3.152 g, 96%) was used in the next step without further purification

Sources & evidence

ORD record
ord-f8b8b66f21a24bb69f480b977e2c80a7
Source dataset
uspto-grants-2001_03
Patent number
US06207660B1

Reaction notes

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