Dimethylformamide → HCID 22463576, compound

HRID 1296381Notes

Reaction equation

HRID 1296381 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:13][N:14]([CH:16]=[O:17])C>N1C=CC=CC=1>[CH3:13][NH:14][C:16]([O:12][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:17]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 5738291,3-Adamantanediol2×

Product 1

HCID 22463576HCID 22463576, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Conditions

Temperature
60 °C

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3-adamantanediol and one drop of pyridine were dissolved in 10 ml of DMF. To the mixture, 20 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-adamantanediol was 99% and 1-(N-methylcarbamoyloxy)-3-adamantanol (yield 90%) was formed.

Workup

  1. additionTo the mixture, 20 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-b20db3975f7240d79e5de499e5f1583b
Source dataset
uspto-grants-2007_07
Patent number
USRE039744E1

Reaction notes

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