Acetic Acid → HCID 72491789, compound

HRID 602600Notes

Reaction equation

HRID 602600 reaction equation
CN(C)CCN.[Cl:7][C:8]1[S:12][C:11]([CH2:13][O:14][N:15]2C(=O)C3=CC=CC=C3C2=O)=[CH:10][CH:9]=1.C(O)(=O)C.[C:30]([C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[NH:40][S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42])(=O)[CH3:31]>CCO>[Cl:39][C:37]1[CH:36]=[CH:35][C:34]([NH:40][S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42])=[C:33]([C:30](=[N:15][O:14][CH2:13][C:11]2[S:12][C:8]([Cl:7])=[CH:9][CH:10]=2)[CH3:31])[CH:38]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 672706502-[(5-Chloro-2-thienyl)methoxy]-1H-isoindole-1,3(2H)-dioneHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

Product 1

HCID 72491789HCID 72491789, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N,N-Dimethylethylenediamine (178 μL, 1.54 mmol) was added to a solution of N-(5-chlorothiophen-2-ylmethoxy)phthalimide (220 mg, 0.75 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h Glacial acetic acid (1 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (211 mg, 0.70 mmol) in EtOH (2 mL), and the mixture stirred for 15 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-(5-chlorothiophen-2-ylmethoxyimino)ethyl]phenyl}trifluoromethanesulfonamide 194 (280 mg, 90%), as white crystals. 1H n.m.r. (400 MHz, CDCl3) δ 11.37, br s, 1H, 7.63, d, J=8.8 Hz, 1H, 7.48, d, J=24 Hz, 1H, 7.33, dd, J=2.4 and 8.8 Hz, 1H, 6.94, d, J=3.8 Hz; 6.81, d, J=3.8 Hz; 5.24, s, 2H, 2.33, s, 3H. HRMS (M+) 445.9540. N-(5-Chlorothiophen-2-ylmethoxy)phthalimide was prepared using the procedure reported in U.S. Pat. No. 4,071,533.

Workup

  1. additionwas then added
  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-1d8f69103d7b44b7a43bc7795922e1f9
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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