Ammonium Chloride → 4-(Trifluoromethyl)thiazole-2-carboximidamide

HRID 388706Notes

Reaction equation

HRID 388706 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:4]=[C:5]([C:8]#[N:9])[S:6][CH:7]=1.CO[Na].[NH4+:15].[Cl-]>CO.C(Cl)Cl>[F:11][C:2]([F:1])([F:10])[C:3]1[N:4]=[C:5]([C:8]([NH2:15])=[NH:9])[S:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 595334344-(Trifluoromethyl)thiazole-2-carbonitrileHCID 178418582HCID 178418582, compound

Product 1

HCID 582827454-(Trifluoromethyl)thiazole-2-carboximidamideYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 285b (28.12 g, 1.0 eq.) in MeOH (13 mL) in an ice/water bath was added MeONa (853 mg, 0.1 eq.) portionwise. The reaction mixture was stirred in the ice/water bath for 15 min and at room temperature for 1 hr. NH4Cl (16.88 g, 2.0 eq.) was then added and the mixture was stirred at room temperature for 4 days. Solvent was removed in vacuo. The solid obtained was suspended in DCM (60 mL) and recovered by filtration. The solid was suspended in MeOH (50 mL) and filtered. The filtrate was concentrated under reduced pressure to yield compound 285 as a white solid in 32% yield. MS (ESI, EI+) m/z=196 (MH+).

Workup

  1. customSolvent was removed in vacuo
  2. customThe solid obtained
  3. filtrationrecovered by filtration
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c601c557ff164cda9eb755424b0375ae
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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