Dichloromethane → HCID 13594136, compound

HRID 2215750Notes

Reaction equation

HRID 2215750 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[Cl-].C[CH:16]=[N+:17]=[CH:18]C.[OH-].[Na+].[CH2:22](Cl)Cl>>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:16][N:17]([CH3:18])[CH3:22])=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27775236-(Trifluoromethyl)indoleHCID 21873455N,N-dimethylmethylene ammonium chloride

Product 1

HCID 13594136HCID 13594136, compoundYield 100%

Procedure

To a solution of 6-trifluoromethylindole (1.0 g, 5.4 mmol) in CH2Cl2 (10 mL) was added N,N-dimethylmethylene ammonium chloride (0.63 g, 6.75 mmol, 1.25 eq.) in one portion and the resultant mixture was stirred at rt for 2 h under N2. 1M NaOH (6.75 mL,) was added, and the reaction mixture was extracted into methylene chloride. The organic layer was washed with aqueous saturated NaCl and dried (MgSO4). The solvent was removed in vacuo to give 1.3 g (100%) of title compound.

Workup

  1. extractionthe reaction mixture was extracted into methylene chloride
  2. washThe organic layer was washed with aqueous saturated NaCl
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-542ae93b444946cbaae81c14d000d3f8
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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