Ammonium Chloride → 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboximidamide

HRID 2174291Notes

Reaction equation

HRID 2174291 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]#[N:16])=[N:6]1.C[O-].[Na+].CO.[Cl-].[NH4+:27].C([O-])(O)=O.[Na+]>>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15](=[NH:27])[NH2:16])=[N:6]1

Participants

5

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 23694274Sodium methanolate methanol2×HCID 690942931-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile

Product 1

HCID 690942961-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboximidamideYield 99%

Procedure

To 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile (Intermediate-5, 0.74 mmol) was added sodium methoxide/MeOH (0.5M, 4 equiv, 5.9 mL). After stirring at ambient temperature for 3 h, additional portion of sodium methoxide/MeOH (1 equiv) was added. After 2 h, ammonium chloride (10 equiv) was added and the resultant mixture was stirred at ambient for 17 h. The reaction mixture was conc. Half-saturated NaHCO3/1N NaOH solution (10:1) was added and the aqueous mixture was extracted with EtOAc. The organic phases were dried over Na2SO4, filtered and conc. to afford 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboximidamide as a white solid (>99% yield).

Workup

  1. waitAfter 2 h
  2. additionwas added
  3. extractionthe aqueous mixture was extracted with EtOAc
  4. dry with materialThe organic phases were dried over Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4063a9721b8b4ca4979c81651b0a0315
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

Loading…