Dimethylformamide → HCID 22463562, compound

HRID 1937260Notes

Reaction equation

HRID 1937260 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(N-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-cddbec2b4d18440c9c5fdda4ee60584c
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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