Benzothiazole → 6-Nitrobenzothiazole

HRID 380607

Reaction equation

HRID 380607 reaction equation
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[CH:11]1>>[N+:1]([C:16]1[CH:17]=[CH:18][C:13]2[N:12]=[CH:11][S:10][C:14]=2[CH:15]=1)([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 7222BenzothiazoleHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 762566-NitrobenzothiazoleYield 79%

Conditions

Temperature
25 °C

Procedure

To a 30 mL solution of 1:1 mixture of HNO3—H2SO4 was added benzothiazole (7.0 mL, 53 mmol) slowly over 1 h period at −25° C. and resulting solution was stirred for 12 h. Reaction temperature was allowed to warm up to 25° C. The reaction mixture was poured into ice water to produce a yellow precipitation which was subjected to column chromatography (CHCl3, neat) to yield 7.3 g (41 mmol, 79%) of the desired product.

Workup

  1. customresulting solution
  2. customReaction temperature
  3. customto produce
  4. customa yellow precipitation which

Sources & evidence

ORD record
ord-047e4bab03954aa0a78ab5ebb53f5f2e
Source dataset
uspto-grants-2001_10
Patent number
US06303643B1

Linked notes

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