Dimethyl Sulfate → HCID 136386384, compound

HRID 634961Notes

Reaction equation

HRID 634961 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]([OH:17])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=[CH:4][C:3]=1[C:18]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH:32]([OH:39])[CH2:33][O:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:26][C:25]=2[OH:40])[N:21]=[C:20]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH:49]([OH:56])[CH2:50][O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:43][C:42]=2[OH:57])[N:19]=1.[OH-].[K+].S(OC)(O[CH3:64])(=O)=O>COCCOCCOC>[OH:57][C:42]1[CH:43]=[C:44]([O:47][CH2:48][CH:49]([OH:56])[CH2:50][O:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH:45]=[CH:46][C:41]=1[C:20]1[N:21]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH:32]([OH:39])[CH2:33][O:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:26][C:25]=2[OH:40])[N:23]=[C:18]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH:10]([OH:17])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:7][C:2]=2[O:1][CH3:64])[N:19]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 135828199HCID 135828199, compound

Product 1

HCID 136386384HCID 136386384, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 11.9 g (15.0 mmol) of 2,4,6-tris[2-hydroxy-4-(3-n-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine in 80 ml of diglyme (Fluka 99.5%) is heated under nitrogen to 80° C. To the solution there are added in succession 1.0 g (15.1 mmol) of pulverized KOH (Fluka, 85%) and 2.5 g (19.8 mmol) of dimethyl sulfate (Fluka, 99%), with stirring. After stirring at 80° C. for 20 h the mixture is cooled, the precipitate is filtered off and the solvent is stripped off from the filtrate. The crude product is purified by column chromatography (silica gel 60, 230-60 mesh, Ø=5 cm, h=30 cm; CH2Cl2/methanol 95:5). Stripping the solvent from the main fraction and drying at 100° C./0.9 mmHg for 3 h give 7.0 g (57.8%) of the title compound (Compound 1).

Workup

  1. stirringAfter stirring at 80° C. for 20 h the mixture
  2. temperatureis cooled
  3. filtrationthe precipitate is filtered off
  4. customThe crude product is purified by column chromatography (silica gel 60, 230-60 mesh, Ø=5 cm, h=30 cm; CH2Cl2/methanol 95:5)
  5. customdrying at 100° C./0.9 mmHg for 3 h

Sources & evidence

ORD record
ord-4167df43a5d6403096d1c61059463314
Source dataset
uspto-grants-2001_02
Patent number
US06184375B2

Reaction notes

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