Ammonia → 7-Nitro-5-pyridin-3-yl-benzothiazol-2-ylamine

HRID 447021Notes

Reaction equation

HRID 447021 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=[C:8]([N+:13]([O-])=O)[C:9]=1[S:10][C:11]#[N:12])([O-:3])=[O:2].N>C(O)(=O)C.O.[Fe]>[N+:1]([C:4]1[C:9]2[S:10][C:11]([NH2:12])=[N:13][C:8]=2[CH:7]=[C:6]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 578136843-(3,5-Dinitro-4-thiocyanato-phenyl)-pyridine

Product 1

HCID 578137647-Nitro-5-pyridin-3-yl-benzothiazol-2-ylamineYield 95.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-(3,5-Dinitro-4-thiocyanato-phenyl)-pyridine (0.66 g, 2.19 mmol) in glacial acetic acid (15 ml) was treated with iron powder (0.61 g, 11.0 mmol) and stirred at ambient temperature for 16 h. The resultant mixture was diluted with water (200 ml) and made alkaline by the addition of concentrated ammonia solution. The solid material was collected by filtration and washed with water followed by ethyl acetate. The filtered solid was then extracted with boiling ethanol (3×200 ml) which was removed in vacuo to give 7-Nitro-5-pyridin-3-yl-benzothiazol-2-ylamine as a pale yellow solid (0.57 g, 95%).

Workup

  1. filtrationThe solid material was collected by filtration
  2. washwashed with water
  3. extractionThe filtered solid was then extracted with boiling ethanol (3×200 ml) which
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-d04cfaebd1ca4acb8f19fe48f270bb74
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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