Dimethylformamide → HCID 22463562, compound

HRID 1296385Notes

Reaction equation

HRID 1296385 reaction equation
[C:1]12([OH:13])[CH2:10][C:5]3([OH:11])[CH2:6][CH:7]([CH2:9][C:3]([OH:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.C[N:15]([CH:17]=[O:18])[CH3:16]>>[CH3:16][NH:15][C:17]([O:13][C:1]12[CH2:10][C:5]3([O:11][C:17](=[O:18])[NH:15][CH3:16])[CH2:6][CH:7]([CH2:9][C:3]([O:12][C:17](=[O:18])[NH:15][CH3:16])([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:18]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 98990221,3,5-Adamantanetriol

Product 1

HCID 22463562HCID 22463562, compoundYield 95%

Conditions

Temperature
60 °C

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3,5-adamantanetriol obtained by the method of Example 32 and one drop of pyridine were dissolved in 10 mL of DMF. To the mixture, 30 mmole of methylisocyanato was added dropwise with stirring. Cooling of the resultant mixture with ice was started at about the time exothermic reaction began. When the exothermic reaction is completed, the mixture was heated to 60° C. and then stirred for one hour. As a result, the conversion of 1,3,5-adamantanetriol was 99% and 1,3,5-tris(methylcarbamoyloxy)adamantane (yield 95%) was obtained.

Workup

  1. additionTo the mixture, 30 mmole of methylisocyanato was added dropwise
  2. customwas started at about the time exothermic reaction
  3. customWhen the exothermic reaction
  4. stirringstirred for one hour

Sources & evidence

ORD record
ord-afe5608e102f414788e9028dfad6a3e7
Source dataset
uspto-grants-2007_07
Patent number
USRE039744E1

Reaction notes

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