Acetic Acid → N-[4-chloro-2-(1-cyclopropylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamide

HRID 602608Notes

Reaction equation

HRID 602608 reaction equation
CN(C)CCN.[CH:7]1([CH2:10][O:11][N:12]2C(=O)C3=CC=CC=C3C2=O)[CH2:9][CH2:8]1.C(O)(=O)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])=[C:30]([C:42](=O)[CH2:43][CH3:44])[CH:29]=1>CCO>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])=[C:30]([C:42](=[N:12][O:11][CH2:10][CH:7]2[CH2:9][CH2:8]2)[CH2:43][CH3:44])[CH:29]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 14843102-(cyclopropylmethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

Product 1

HCID 73036091N-[4-chloro-2-(1-cyclopropylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(cyclopropylmethoxy)phthalimide (326 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4, followed by the addition of a solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (316 mg, 1.0 mmol) in EtOH (2 mL), and the mixture stirred for 65 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1) to afford N-[4-chloro-2-(1-cyclopropylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamide 196 (205 mg, 53%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 11.88, br s, 1H, 7.66, d, J=8.8 Hz, 1H, 7.49, d, J=2.4 Hz, 1H, 7.33, dd, J=2.4 and 8.8 Hz, 1H, 4.02, d, J=7.2 Hz, 1H, 2.83, q, J=7.6 Hz, 2H, 1.22, m, 4H, 0.64, m, 2H, 0.33, m, 2H. HRMS (M+) 384.0515. N-(cyclopropylmethoxy)phthalimide was prepared by the procedure described in Example 1G.

Workup

  1. stirringthe mixture stirred for 65 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1)

Sources & evidence

ORD record
ord-e2f001c2adc04bb5bf27a4509da1460d
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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