Sodium Acetate → N-{4-chloro-2-[(4-fluorophenoxyimino)cyclohexylmethyl]phenyl}trifluoromethanesulfonamide

HRID 970880Notes

Reaction equation

HRID 970880 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=O)[CH:3]=1.Cl.[F:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][NH2:33])=[CH:28][CH:27]=1.CC([O-])=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([C:16](=[N:33][O:32][C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:3]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 67270465N-(4-chloro-2-cyclohexanecarbonylphenyl)trifluoromethanesulfonamide

Product 1

HCID 72491672N-{4-chloro-2-[(4-fluorophenoxyimino)cyclohexylmethyl]phenyl}trifluoromethanesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloro-2-cyclohexanecarbonylphenyl)trifluoromethanesulfonamide 29E (410 mg, 1.11 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (200 mg, 1.22 mmol) and anhydrous NaOAc (100 mg, 1.22 mmol) in EtOH (20 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue purified by column chromatography (eluting with CH2Cl2/PE, 3:7 to CH2Cl2) to afford N-{4-chloro-2-[(4-flurophenoxyimino)cyclohexylmethyl]phenyl}trifluoromethanesulfonamide 169 (200 mg, 38%), as a white solid. 1H n.m.r. (200 MHz, CDCl3) δ 7.54, d, J=8.8 Hz, 1H; 7.43, dd, J=2.2 and 8.8 Hz, 1H; 7.24, d, J=2.2 Hz, 1H; 7.12-6.95, m, 5H; 2.56, m, 1H; 2.14, m, 1H; 1.93-1.65, m, 5H; 1.29, m, 4H.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 3:7 to CH2Cl2)

Sources & evidence

ORD record
ord-248d905b6c97432e9f4e1a31f53c9c04
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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