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Trichloroacetonitrile → 2-(trichloromethyl)-1H-imidazole

HRID 709928
Notes
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Reaction equation

HRID 709928 reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].CO[CH:9](OC)[CH2:10][NH2:11]>C1COCC1>[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]1[NH:11][CH:10]=[CH:9][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11011TrichloroacetonitrileHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 100811212-(trichloromethyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trichloroacetonitrile (28.8 g, 200 mmol, 1 eq) in anhydrous THF (70 mL) at −60° C. under an argon atmosphere, 2,2-dimethoxyethanamine (C-1) (21.8 mL, 200 mmol, 1.0 eq) is added dropwise over 5 min. The resulting mixture is allowed to warm to RT and stirred at RT for 4 h. The mixture is concentrated in vacuo and the residue is added in portions to a stirred solution of trifluoroacetic acid (100 mL) at −30° C. under argon. The resulting mixture is then stirred from −30° C. to RT overnight. The reaction mixture is concentrated in vacuo to afford the product, 2-(trichloromethyl)-1H-imidazole (C-2). The product is used in the next step without further purification.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionthe residue is added in portions to a stirred solution of trifluoroacetic acid (100 mL) at −30° C. under argon
  3. stirringThe resulting mixture is then stirred from −30° C. to RT overnight
  4. concentrationThe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-19eedc643924499f85843ebf2d754d99
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181221B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes