Benzonitrile, 4-(trifluoromethyl)- → HCID 11213981, compound

HRID 1786777Notes

Reaction equation

HRID 1786777 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[C:19]([O:23][C:24](=[O:42])[C:25]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][C:38]([NH:40][NH2:41])=O)=[CH:31][CH:30]=1)([CH3:27])[CH3:26])([CH3:22])([CH3:21])[CH3:20]>CO>[C:19]([O:23][C:24](=[O:42])[C:25]([CH3:27])([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][C:38]2[NH:40][N:41]=[C:7]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:10][CH:9]=3)[N:8]=2)=[CH:31][CH:30]=1)[CH3:26])([CH3:21])([CH3:20])[CH3:22]

Participants

5

Reactant 3

HCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 112446042-[4-(3-Hydrazinocarbonyl-propyl)-phenoxy]-2-methyl-propionic acid tert-butyl esterHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 11213981HCID 11213981, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 4-(trifluoromethyl)benzonitrile (0.51 g, 3.0 mol) and potassium tert-butoxide (0.023 g, 0.21 mmol) to a solution of 2-[4-(3-Hydrazinocarbonyl-propyl)-phenoxy]-2-methyl-propionic acid tert-butyl ester (0.5 g, 1.5 mmol) in MeOH (5 mL). Stir the mixture at reflux overnight. Add an additional 0.2 equivalents of potassium tert-butoxide and stir the reaction for 24 h. Quench the crude with water, remove the MeOH in vacuo, and extract the aqueous layer with EtOAc. Separate the organic layer, dry with MgSO4, and concentrate in vacuo. Purify the crude by Biotage (Hexane/EtOAc 4:1) yielding 0.32 g (44%) of the title compound, example 10 as a pale yellow oil. MS Data (ES+) m/z 490.6 [M+H]

Workup

  1. temperatureat reflux overnight
  2. stirringstir
  3. customthe reaction for 24 h
  4. customQuench the crude with water
  5. customremove the MeOH in vacuo
  6. extractionextract the aqueous layer with EtOAc
  7. customSeparate the organic layer
  8. dry with materialdry with MgSO4
  9. concentrationconcentrate in vacuo
  10. customPurify the crude by Biotage (Hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-7788c714a3ec42c6a0a288db6f361c05
Source dataset
uspto-grants-2009_03
Patent number
US07507832B2

Reaction notes

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