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Ethanol → 2-Amino-3-(5-chlorobenzotriazol-1-yl)-2-methylpropionitrile

HRID 7217
Notes
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Reaction equation

HRID 7217 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH2:9]C(=O)C)[N:7]=[N:8][C:4]=2[CH:3]=1.[C-:15]#[N:16].[Na+].[Cl-].[NH4+:19].[CH2:20](O)[CH3:21]>N>[NH2:19][C:20]([CH3:21])([CH2:9][N:6]1[C:5]2[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=[N:7]1)[C:15]#[N:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 220202531-(5-Chlorobenzotriazol-1-yl)-propan-2-one

Product 1

HCID 220202682-Amino-3-(5-chlorobenzotriazol-1-yl)-2-methylpropionitrile

Reagents, catalysts & solvents 1

HCID 222
Ammonia
Solvent

Procedure

240 mg of 1-(5-chlorobenzotriazol-1-yl)-propan-2-one are dissolved in 4 ml of a 2-molar solution of ammonia in ethanol, then 64 mg of sodium cyanide and 91 mg of ammonium chloride are added and the mixture is stirred over night at room temperature. The reaction mixture is subsequently concentrated by evaporation in a vacuum, dissolved again in ethyl acetate, and washed with water and saturated sodium chloride solution. The organic phase is separated, dried with magnesium sulphate and concentrated by evaporation. 2-amino-3-(5-chlorobenzotriazol-1-yl)-2-methylpropionitrile is thus obtained.

Workup

  1. concentrationThe reaction mixture is subsequently concentrated by evaporation in a vacuum
  2. dissolutiondissolved again in ethyl acetate
  3. washwashed with water and saturated sodium chloride solution
  4. customThe organic phase is separated
  5. dry with materialdried with magnesium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7ed350118fc746a58b79ffe1365ea045
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084280B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes