Water → HCID 66647247, compound

HRID 536734Notes

Reaction equation

HRID 536734 reaction equation
[CH:1]1([CH2:5][NH:6][C:7]#[N:8])[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].O>COCCOC>[C:18]([C:17]1[O:22][C:7](=[NH:8])[N:6]([CH2:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)[CH:16]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 20434476HCID 20434476, compound

Product 1

HCID 66647247HCID 66647247, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(cyclobutylmethyl)cyanamide (0.40 g, 3.6 mmol), cesium carbonate (2.4 g, 7.3 mmol) and 1-bromo-3,3-dimethylbutan-2-one (0.50 mL, 3.6 mmol, Aldrich) in 1,2-dimethoxyethane (20 mL) was heated to 80° C. overnight. The mixture was poured into water, and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, concentrated under reduced pressure to provide the title compound (0.6 g). LCMS (APCI+) m/z 209 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b0e843e30eb43d4a502715ec5fbf94d
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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