Triethylamine → HCID 178513303, compound

HRID 624648Notes

Reaction equation

HRID 624648 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8]C(C#N)=[C:4]([F:10])[CH:3]=1.Cl.[NH2:12][OH:13].CC[N:16]([CH2:19][CH3:20])CC>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:20]([C:19](=[NH:16])[NH:12][OH:13])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 936554-Chloro-2-fluorobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513303HCID 178513303, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-chloro-2-fluorobenzonitrile 38 (400 g, 2.58 mol, 1.0 eq), hydroxylamine hydrochloride (448 g, 6.45 mol, 2.5 eq) in MeOH (1 L, 2.5 vol) was added Et3N (313 g, 3.1 mol, 1.2 eq), then the mixture was stirred at 60° C. for 40 min and checked by HPLC (no nitrile remaining) Reaction was then quenched by H2O (10 L), and lots of off-white solid was separated out, and then filtered, the filter cake was washed with water (10 L×2) and 378 g 4-chloro-2-fluoro-N-hydroxybenzimidamide 39 was obtained with 93% purity (Scheme 15).

Workup

  1. customReaction
  2. customwas then quenched by H2O (10 L), and lots of off-white solid
  3. customwas separated out
  4. filtrationfiltered
  5. washthe filter cake was washed with water (10 L×2)

Sources & evidence

ORD record
ord-9e164b3994a34521a214880cd629114a
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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