Methanesulfonamide → N-(cyclopropylmethylene)methanesulfonamide

HRID 1897814Notes

Reaction equation

HRID 1897814 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-6553aa83d5944cd6808fe53f17c3c8bc
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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