Triethylamine → HCID 54544190, compound

HRID 1835020Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:11]#[N:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>O1CCCC1>[CH3:20][S:21]([O:1][N:2]=[C:3]([C:11]#[N:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)(=[O:23])=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

33.6 g (0.21 mol) of α-hydroxyimino-4-methylbenzylcyanide and 31.9 g (0.31 mol) of triethylamine are dissolved in 425 ml of tetrahydrofuran and to this solution is then added dropwise a solution of 26.44 g (0.23 mol) of methanesulfonyl chloride at 0-5° C. After the addition is complete, the mixture is stirred for 30 minutes at 0° C. and then overnight at room temperature. Subsequently, the reaction mixture is filtered and the filtrate is washed with a saturated sodium chloride solution and dried over magnesium sulfate. The solvent is then distilled off on a rotary evaporator, giving a solid residue which is recrystallised from toluene. 37.3 g (75%) of α-(methylsulfonyloxyimino)-4-methylbenzylcyanide are obtained in the form of a colourless powder having an m.p. of 97.5-102.5° C. The 1H-NMR spectrum shows it to be a pure stereoisomer.

Workup

additionAfter the addition
customovernight
customat room temperature
filtrationSubsequently, the reaction mixture is filtered
washthe filtrate is washed with a saturated sodium chloride solution
dry with materialdried over magnesium sulfate
distillationThe solvent is then distilled off on a rotary evaporator
customgiving a solid residue which
customis recrystallised from toluene

Sources & evidence

ORD record: ord-f9c91af27eb34899a6908f3b994f1800
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770420B2

Reaction notes

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