Acetic Acid → HCID 72491789, compound

HRID 970859Notes

Reaction equation

HRID 970859 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=2.4 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.

Workup

  1. stirringthe mixture stirred for 15 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-ab254eb43b1d42d29310945e922539a0
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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