m-Chloroperbenzoic acid → HCID 59707964, compound

HRID 1010507Notes

Reaction equation

HRID 1010507 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][N:7]([CH2:14][CH2:15][O:16][CH2:17][O:18][CH3:19])[CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13].ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[CH3:19][O:18][CH2:17][O:16][CH2:15][CH2:14][N+:7]([O-:28])([CH2:6][CH2:5][O:4][CH2:3][O:2][CH3:1])[CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 218723762-(Methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amine

Product 1

HCID 59707964HCID 59707964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

28.1 g (0.1 mole) of tris(2-(methoxymethoxy)ethyl)-amine was dissolved in 85 g of dichloromethane, which was ice cooled. To the solution, 26.5 g (0.1 mole) of 65% pure m-chloroperbenzoic acid in 250 g of dichloromethane was added dropwise at such a rate that the mixture might not exceed 5° C. The mixture was allowed to mature for one hour at room temperature. The reaction solution was concentrated below 30° C. and the residue was purified by column chromatography (basic alumina, elute; dichloromethane/methanol). The eluate was concentrated whereupon the desired compound solidified. The amount was 27.3 g and the yield was 92*.

Workup

  1. temperaturecooled
  2. customexceed 5° C
  3. concentrationThe reaction solution was concentrated below 30° C.
  4. customthe residue was purified by column chromatography (basic alumina, elute; dichloromethane/methanol)
  5. concentrationThe eluate was concentrated whereupon the desired compound

Sources & evidence

ORD record
ord-af6211ce87024d03a795ac4134b96c8d
Source dataset
uspto-grants-2011_07
Patent number
US07977027B2

Reaction notes

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