Triethylamine → HCID 53671357, compound

HRID 1835017Notes

Reaction equation

HRID 1835017 reaction equation
[OH:1][N:2]=[C:3]([C:12]#[N:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O1CCCC1.C(Cl)Cl>[CH3:21][S:22]([O:1][N:2]=[C:3]([C:12]#[N:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 43981912-hydroxyimino-2-(4-methoxyphenyl)acetonitrile

Product 1

HCID 53671357HCID 53671357, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

20 g (0.114 mol) of α-hydroxyimino-4-methoxybenzylcyanide are dissolved in 100 ml of tetrahydrofuran (THF) and charged with 17.2 g (0.17 mol) of triethylamine. To this mixture are added dropwise and with cooling 14.3 g (0.0.12 mol) of methanesulfonyl chloride dissolved in 50 ml of THF. This mixture is then warmed to room temperature and stirred for 12 hours. Subsequently, the reaction solution is diluted with 300 ml of CH2Cl2, washed with water, dilute hydrochloric acid and again with water and is then dried over magnesium sulfate. After filtration, the solvent is distilled off on a rotary evaporator and the brownish crude product is recrystallised from toluene, giving 23.9 g (83%) of α-(methyl-sulfonyloxy-imino)-4-methoxybenzylcyanide in the form of beige crystals having an m.p. of 124-125° C. The 1H-NMR spectrum of the compound shows the product to be a pure stereoisomer.

Workup

  1. additionTo this mixture are added dropwise
  2. washwashed with water, dilute hydrochloric acid and again with water
  3. dry with materialis then dried over magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent is distilled off on a rotary evaporator
  6. customthe brownish crude product is recrystallised from toluene

Sources & evidence

ORD record
ord-fd9cac2e1d0c46bda2c065ae796f9273
Source dataset
uspto-grants-2004_08
Patent number
US06770420B2

Reaction notes

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