Nitric Acid → 6-Methoxy-5-nitro-2-(pyridin-2-yl)-1,3-benzothiazole

HRID 1287834Notes

Reaction equation

HRID 1287834 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[S:9][C:5]=2[CH:4]=1.[N+:18]([O-])([OH:20])=[O:19].[OH-].[Na+]>OS(O)(=O)=O>[N+:18]([C:17]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[N:7][C:6]=2[CH:16]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 215066886-Methoxy-2-(pyridin-2-yl)-1,3-benzothiazole

Product 1

HCID 215066866-Methoxy-5-nitro-2-(pyridin-2-yl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

6-Methoxy -2-(pyridinyl)benzothiazole, 30 g, (0.124 mole) is dissolved in 115 cc of concentrated H2SO4 and cooled to 0°. Nitric acid, 7.9 cc (0.124 mole) is added and the solution stirred for 2 hours at room temperature. The reaction mixture is poured on ice and the pH adjusted to 10 with 50% NaOH solution. The precipitate is filtered and dried to yield 11 g of product.

Workup

  1. temperaturecooled to 0°
  2. additionThe reaction mixture is poured on ice
  3. filtrationThe precipitate is filtered
  4. customdried

Sources & evidence

ORD record
ord-f39473ce744d4053b8de0f76a348e28c
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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