3-(Trifluoromethyl)aniline → HCID 1214264, compound

HRID 1446673Notes

Reaction equation

HRID 1446673 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:33][C:34]([F:43])([F:42])[C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38]>O1CCCC1.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:38][C:37]2[CH:39]=[CH:40][CH:41]=[C:35]([C:34]([F:33])([F:42])[F:43])[CH:36]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 682631,1'-CarbonyldiimidazoleHCID 74654Benzeneacetic acid, 4-bromo-HCID 81531Diisopropylethylamine

Product 1

HCID 1214264HCID 1214264, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-bromophenylacetic acid (10.00 g, 46.50 mmol), diisopropylethylamine (12.02 g, 16.20 mL, 93.00 mmol) and 1,1′-carbonyldiimidazole (8.29 g, 51.15 mmol) in tetrahydrofuran (200 mL) at room temperature. Stir the contents under nitrogen for one hour. Add m-trifluoromethylaniline (15.00 g, 93.00 mmol) and stir the reaction overnight at room temperature. Concentrate the reaction to near dryness, dissolve in dichloromethane (250 mL) and extract with 2 N NaOH (200 mL), water (100 mL) and 1 N HCl (2×200 mL). Wash the organic layer with saturated aqueous saturated sodium chloride (100 mL), dry over MgSO4, filter and concentrate. Dry load the material onto silica (100 g) and chromatograph on silica using dichloromethane as eluent to yield the product (13.00 g, 78.1%). MS(ES), m/z 356/358 (M+1).

Workup

  1. customthe reaction overnight at room temperature
  2. concentrationConcentrate
  3. customthe reaction
  4. extractionextract with 2 N NaOH (200 mL), water (100 mL) and 1 N HCl (2×200 mL)
  5. washWash the organic layer with saturated aqueous saturated sodium chloride (100 mL)
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customDry load the material onto silica (100 g) and chromatograph on silica

Sources & evidence

ORD record
ord-de90e1d1acb74642b5ed92aa4ff28e1f
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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