Ammonium Chloride → 2-Thiazolo[4,5-c]pyridin-2-yl-phenylamine

HRID 1667031Notes

Reaction equation

HRID 1667031 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1)([O-])=O.[NH4+].[Cl-]>CO.O.[Fe]>[S:11]1[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=[C:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 596801882-(2-Nitrophenyl)thiazolo[4,5-c]pyridine

Product 1

HCID 596799612-Thiazolo[4,5-c]pyridin-2-yl-phenylamineYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A suspension of 2-(2-nitrophenyl)thiazolo[4,5-c]pyridine (1.170 g, 4.6 mmol), Fe powder (1.26 g, 22.8 mmol) and NH4Cl (1.97 g, 36.8 mmol) in CH3OH: H2O (4:1, 80 mL) was refluxed for 6 hrs. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was poured into water. The precipitate was collected by filtration, and washed with water (20 mL×3) to afford 2-thiazolo[4,5-c]pyridin-2-yl-phenylamine as a yellow solid (0.760 g, yield: 73%).

Workup

  1. temperaturewas refluxed for 6 hrs
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. additionThe residue was poured into water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water (20 mL×3)

Sources & evidence

ORD record
ord-42185bba297f4aae87056c47fa096c17
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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