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

HRID 1010653Notes

Reaction equation

HRID 1010653 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-ee0671df6b3b454e811b6b6ee6b89e11
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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