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

HRID 880804Notes

Reaction equation

HRID 880804 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-7a9b2327914b40e8815243dfc1d362f2
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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