Trifluoroacetic acid → 5-[2-(4-Chlorophenyl)ethyl]-2-(3,5-dichlorophenyl)tetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

HRID 49983

Reaction equation

HRID 49983 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]([CH2:23]OC)[CH2:18][Si](C)(C)C)=[CH:11][CH:10]=1.[Cl:26][C:27]1[CH:28]=[C:29]([N:34]2[C:38](=[O:39])[CH2:37][CH2:36][C:35]2=[O:40])[CH:30]=[C:31]([Cl:33])[CH:32]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][N:17]2[CH2:18][CH:37]3[C:38](=[O:39])[N:34]([C:29]4[CH:28]=[C:27]([Cl:26])[CH:32]=[C:31]([Cl:33])[CH:30]=4)[C:35](=[O:40])[CH:36]3[CH2:23]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90363DimethachlonHCID 213010074-Chloro-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzeneethanamine

Product 1

HCID 213010105-[2-(4-Chlorophenyl)ethyl]-2-(3,5-dichlorophenyl)tetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To prepare the compound of formula (Im), wherein R11 is chloro and m is 2, TFA (32 μl, 0.41 mmol) was added to an ice-cooled mixture of 4-chloro-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzeneethanamine (1.5 g, 5.25 mmol) (Preparation 14) and N-(3,5-dichlorophenyl)succinimide (1 g, 4.13 mmol, prepared according to Fujinami et al., Agr. Biol. Chem. [1972], p. 318, incorporated herein by reference) in methylene chloride (10 mL). The reaction mixture was allowed to warm to RT over 3 h. The solution was washed with ammonium hydroxide. The organic layer was dried over MgSO4 and concentrated in vacuo to afford after chromatography over silica gel (CH2Cl2) the above-referenced compound as a white solid (1.56 g). Mp=115° C. 1H NMR (CDCl3): 7.40 (1H, br s), 7.15-7.35 (4H, m), 7.07 (2H, d, J=8.3 Hz), 3.4-3.5 (2H, m), 3.3-3.4 (2H, m), 2.55-2.8 (4H, m), 2.35-2.5 (2H, m).

Workup

  1. customTo prepare the compound of formula (Im), wherein R11
  2. temperaturecooled
  3. customprepared
  4. washThe solution was washed with ammonium hydroxide
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-baad0f8c5728421b9d32f6e582adfc5c
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Linked notes

Loading…