Toluene → HCID 12822285, compound

HRID 2163345Notes

Reaction equation

HRID 2163345 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[C:8]1([CH:14]([N:16]2[CH2:19][CH:18](O)[CH2:17]2)[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CS(Cl)(=O)=O.[H-].[Na+].[C:28]1(C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1C=CC=CC=1>[C:8]1([C:7]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([CH:18]2[CH2:19][N:16]([CH:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:15])[CH2:17]2)[C:6]#[N:3])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 37924881-(1-phenylethyl)azetidin-3-ol

Product 1

HCID 12822285HCID 12822285, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 67.9 g. (0.67 mole) of triethylamine and 114 g. (0.64 mole) of 1-(1-phenylethyl)-3-azetidinol in 800 ml. of dry benzene was added dropwise 73.6 g. (0.65 mole) of methane sulfonylchloride while cooling in an ice bath. After stirring two hours at room temperature the mixture was filtered. The filtrate was added dropwise over a 40-minute period to a refluxing suspension of the sodium salt of diphenylacetonitrile prepared by refluxing 123.5 g. (0.64 mole) of the nitrile and 28.2 g. (0.7 mole) of 57% sodium hydride in 1 liter of dry toluene for 2.5 hrs. The toluene solution was extracted with dilute hydrochloric acid. The toluene-organic layer was treated with water and a volume of isooctane equal to the toluene layer. The oily layer and aqueous layer were separated together. The toluene layer was washed several times with water. All aqueous layers (and the oil) were combined and basified with dilute sodium hydroxide and extracted with chloroform. The chloroform layer was dried over sodium sulfate and concentrated by distillation. The residue was crystallized from isooctane isopropyl ether to give 94 g. (42%) of product melting 122°-130° C.

Workup

  1. filtrationwas filtered
  2. additionThe filtrate was added dropwise over a 40-minute period to a refluxing suspension of the sodium salt of diphenylacetonitrile
  3. customprepared
  4. temperatureby refluxing 123.5 g
  5. extractionThe toluene solution was extracted with dilute hydrochloric acid
  6. additionThe toluene-organic layer was treated with water
  7. customThe oily layer and aqueous layer were separated together
  8. washThe toluene layer was washed several times with water
  9. extractionextracted with chloroform
  10. dry with materialThe chloroform layer was dried over sodium sulfate
  11. concentrationconcentrated by distillation
  12. customThe residue was crystallized from isooctane isopropyl ether
  13. customto give 94 g
  14. custommelting 122°-130° C.

Sources & evidence

ORD record
ord-e8d8a25998d248e3bc92e3930264f07c
Source dataset
uspto-grants-1979_01
Patent number
US04133881

Reaction notes

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