Triethylamine → HCID 53671357, compound

HRID 376815Notes

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.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>O1CCCC1>[CH3:24][S:21]([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:23])=[O:22]

Participants

Conditions

Temperature: -5 °C

Procedure

α-(Methylsulfonyloxyimino)-4-methoxybenzyl cyanide was prepared in the following manner. Thus, 51.0 g (0.29 mole) of α-hydroxyimino-4-methoxybenzyl 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 36.5 g (0.32 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 73.6 g of a solid residue as a crude product which was purified by repeating recrystallization from acetonitrile to give 47.5 g of a white crystalline product having a melting point of 116° C., which could be identified to be the target compound from the results of the analysis described below. The above mentioned yield of the product corresponds to 64.5% of the theoretical value.

Workup

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

Sources & evidence

ORD record: ord-ee3b604dc0fe47f4b94ef3a22478dc5e
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022666

Reaction notes

Loading…