4-Toluenesulfonyl chloride → Ethyl 4-({[(4-methylphenyl)sulfonyl]oxy}imino)cyclohexanecarboxylate

HRID 1620631Notes

Reaction equation

[OH:1][N:2]=[C:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:1][N:2]=[C:3]2[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 4-(hydroxyimino)cyclohexanecarboxylate (1.85 g) in pyridine (10 mL) was added 4-methylbenzenesulfonyl chloride (2.28 g) over 5-10 min at −20° C. The reaction mixture was stirred for several hours while allowing to gradually warm to 0° C. The reaction mixture was added to ice water, and the precipitate was collected by filtration, and washed with ice water to give the title compound (2.54 g).

Workup

filtrationthe precipitate was collected by filtration
washwashed with ice water

Sources & evidence

ORD record: ord-88962a8c3843494fad143cd7da945890
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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