Nitric Acid → 2-Methyl-7-nitro-1,3-benzothiazole-5,6-diol

HRID 1881176Notes

Reaction equation

HRID 1881176 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[C:8]([OH:12])=[CH:7][C:5]=2[N:6]=1.[N+:13]([O-])([OH:15])=[O:14]>C(OCC)(=O)C.ClCCl>[CH3:1][C:2]1[S:3][C:4]2[C:10]([N+:13]([O-:15])=[O:14])=[C:9]([OH:11])[C:8]([OH:12])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 7369402-methyl-1,3-benzothiazole-5,6-diol

Product 1

HCID 159831022-Methyl-7-nitro-1,3-benzothiazole-5,6-diol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-benzothiazole-5,6-diol was dissolved in ethyl acetate and a solution of nitric acid in dichloromethane (2M, 0.38 ml) was gradually added at 20° C. into. The solution was stirred 10 min at room temperature and then it was poured into ice water and extracted into ethyl acetate and evaporated. The product was purified by column chromatography using toluene-ethyl acetate-acetic acid 8:1:1 as the eluent.

Workup

  1. extractionextracted into ethyl acetate
  2. customevaporated
  3. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-93c972d9802948868638b6370fcf9ec8
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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