Water → HCID 67945520, compound

HRID 728306Notes

Reaction equation

HRID 728306 reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].C([Li])CCC.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:22]#[N:23])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.O>O1CCCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:22]([NH2:23])=[CH:1][S:2]([CH3:5])(=[O:4])=[O:3])[CH2:21][CH2:20][CH2:19]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6213Dimethyl SulfoneHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 178418339Butyllithium

Product 1

HCID 67945520HCID 67945520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dimethylsulphone (8.3 g), in dry tetrahydrofuran (150 ml) was added dropwise to a stirred ice-cold solution of butyllithium (30 ml of 2.6M solution in hexane). The mixture was stirred at room temperature for 15 minutes and then a solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (15 g) in tetrahydrofuran (25 ml) was added over 15 minutes and the resulting solution was heated under reflux for 16 hours. The solution was cooled and treated with water and the organic layer separated. The aqueous layer was extracted with ether and the ether extracts combined with the previously separated organic layer, dried and the solvents were removed by evaporation. The resulting oil crystallised, and the solid was washed with petroleum ether (b.p. 40°-60° C.) to give 1-[1-(4-chlorophenyl)cyclobutyl]-2-methylsulphonylvinylamine (m.p. 125°-126° ).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureThe solution was cooled
  4. customthe organic layer separated
  5. extractionThe aqueous layer was extracted with ether
  6. customdried
  7. customthe solvents were removed by evaporation
  8. customThe resulting oil crystallised
  9. washthe solid was washed with petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-c320e787a34d47c2857e674bb1fc6ff1
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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