Triethylamine → HCID 54463590, compound

HRID 376816Notes

Reaction equation

HRID 376816 reaction equation
[OH:1][N:2]=[C:3]([C:10]#[N:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>O1CCCC1>[CH3:22][S:19]([O:1][N:2]=[C:3]([C:10]#[N:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 699982-(Hydroxyimino)-2-phenylacetonitrile

Product 1

HCID 54463590HCID 54463590, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

α-(Methylsulfonyloxyimino)benzyl cyanide was prepared in the following manner. Thus, 52.5 g (0.36 mole) of α-hydroxyiminobenzyl cyanide and a solution prepared by dissolving 44.0 g (0.43 mole) of triethylamine in 400 ml of tetrahydrofuran were introduced into a reaction vessel to form a uniform solution which was chilled to and kept at -5° C. Into the solution in the reaction vessel were added dropwise 49.0 g (0.43 mole) of mesyl chloride over a period of 2 hours under agitation. The reaction mixture in the vessel was agitated at -5° C. for 3 hours and then at about 10° C. for additional 2 hours. The reaction mixture was freed from tetrahydrofuran as the solvent by distillation under reduced pressure at 30° C. to give 75.0 g of a solid residue which was purified by repeating recrystallization from acetonitrile to give 64.5 g of a white crystalline product having a melting point of 120° C., which could be identified to be the target compound from the results of the analysis described below and coincidence of the melting point with the known value reported in literatures. The above mentioned yield of the product corresponds to 80.0% of the theoretical value.

Workup

  1. additionwere introduced into a reaction vessel
  2. customto form a uniform solution which
  3. temperaturewas chilled to and
  4. customkept at -5° C
  5. waitat about 10° C. for additional 2 hours
  6. distillationThe reaction mixture was freed from tetrahydrofuran as the solvent by distillation under reduced pressure at 30° C.

Sources & evidence

ORD record
ord-5488614a8a224a7a928cc795cc408f2f
Source dataset
uspto-grants-2000_02
Patent number
US06022666

Reaction notes

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