Methanesulfonamide → N-(cyclopropylmethylene)methanesulfonamide

HRID 2407442

Reaction equation

HRID 2407442 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[CH3:6][S:7]([NH2:10])(=[O:9])=[O:8]>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:1]1([CH:4]=[N:10][S:7]([CH3:6])(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 72879MethanesulfonamideHCID 123114Cyclopropanecarboxaldehyde

Product 1

HCID 66788560N-(cyclopropylmethylene)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of cyclopropanecarbaldehyde (0.374 mL, 5 mmol) and methanesulfonamide (0.523 g, 5.5 mmol) in toluene (15 mL) was added titanium(IV) isopropoxide (2.93 mL, 10 mmol), and the mixture was heated to 100° C. for 1 day. The mixture was cooled to room temperature and concentrated in vacuo. The residue was placed under high vacuum for 30 min to give a biphasic mixture. The top layer was discarded. The residue was used in next step without further purification.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a biphasic mixture
  4. customThe residue was used in next step without further purification

Sources & evidence

ORD record
ord-84149e9e913b4034acc523b218491be1
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Linked notes

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