Ethanol → 2-Methyl-4-methoxy-5-(2-hydroxypropyl)aminophenyl mesylate

HRID 2050756Notes

Reaction equation

HRID 2050756 reaction equation
[S:1]([O:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])(=[O:4])(=[O:3])[CH3:2].[CH2:16]([OH:18])[CH3:17].[CH2:19]1[O:22][CH:20]1[CH3:21].[CH:23](Cl)(Cl)Cl.C(OCC)(=O)C>>[S:1]([O:5][C:6]1[CH:11]=[C:10]([NH:12][CH2:19][CH:20]([OH:22])[CH3:21])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])(=[O:4])(=[O:3])[CH3:2].[S:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]([CH2:19][CH:20]([OH:22])[CH3:21])[CH2:17][CH:16]([OH:18])[CH3:23])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])(=[O:4])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 6378Propylene OxideHCID 198211482-Methyl-4-methoxy-5-aminophenyl mesylateHCID 21584013Chloroform ethylacetate

Product 2

HCID 198211302-Methyl-4-methoxy-5-bis(2-hydroxypropyl)aminophenyl mesylateYield 16%HCID 198211542-Methyl-4-methoxy-5-(2-hydroxypropyl)aminophenyl mesylateYield 69%

Conditions

Temperature
70 °C

Procedure

7.52 g (32.6 mmol) of 2-methyl-4-methoxy-5-aminophenyl mesylate, 90 ml of ethanol and 4.2 ml (3.5 g, 60 mmol) of propylene oxide were fed into an autoclave (200 ml) and the mixture was stirred at 70° C. for 35 hours. After allowing to cool, the solvent was distilled off under reduced pressure to obtain a brown oily matter. The oily matter thus obtained was subjected to silica gel chromatography (Silica Gel 60, trade name, manufactured by Merck Co., 70-230 mesh, 300 g, eluent: chloroform/ethyl acetate (1:1 by volume)), and thereby give 0.33 g (1.4 mmol, 6%) of the starting material from the first fraction, 6.46 g (22.4 mmol, 69%) of 2-methyl-4-methoxy-5-(2-hydroxypropyl)aminophenyl mesylate from the second fraction in the form of an oily matter and 1.81 g (5.2 mmol, 16%) of 2-methyl-4-methoxy-5-bis(2-hydroxypropyl)aminophenyl mesylate from the third fraction in the form of brown crystals.

Workup

  1. temperatureto cool
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain a brown oily matter
  4. customThe oily matter thus obtained

Sources & evidence

ORD record
ord-c3f11f80293842f4961844c2616a24ad
Source dataset
uspto-grants-1991_05
Patent number
US05015260

Reaction notes

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