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Triethylamine → HCID 19029324, compound

HRID 2256321
Notes
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Reaction equation

HRID 2256321 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:15][C:14](=[O:16])[O:13][C:11](=[O:12])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22][NH2:23].[CH2:33](N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([N:23]([CH2:22][C:21]2[CH:20]=[C:19]([C:18]([F:31])([F:32])[F:17])[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=2)[CH3:33])=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dione

Product 1

HCID 19029324HCID 19029324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(3,4-Dichlorophenyl)glutaric anhydride (3.1 g, Example 1, Step C) in CH2Cl2 (50 mL) at 0° C. was treated sequentially with 3,5-bis-(trifluoromethyl)benzylamine (3.4 g), triethylamine (1.83 mL) and N,N-dimethylaminopyridine (150 mg). The mixture was stirred at 0° C. for two hours then allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was diluted with CH2Cl2 (200 mL) and washed with 1N HCl (1×100 mL) and water (1×100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (6.1 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washwashed with 1N HCl (1×100 mL) and water (1×100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8cda20053ef342ac8ecff8ba13052a99
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05654316

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes