Nitric Acid → 2-(Methoxymethyl)-6-nitro-1,3-benzothiazole

HRID 389573Notes

Reaction equation

HRID 389573 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 40645242-(Methoxymethyl)-1,3-benzothiazole

Product 1

HCID 667601042-(Methoxymethyl)-6-nitro-1,3-benzothiazoleYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-methoxymethyl-benzothiazole (2.4 g, 13.4 mmol) in concentrated sulfuric acid (8 mL) was added a mixture of 90% fuming nitric acid (2 mL) and concentrated sulfuric acid (1.3 mL) at a rate to keep the internal temperature below 5° C. After the addition was completed, the reaction mixture was stirred for 15 min at 0° C. and then at RT for 2 h. The mixture was poured into ice cold water. Collection of the precipitated solid by filtration, washing with cold water until the pH of the eluent was neutral, afforded 2.6 g (79%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.8 (d, J=2.1 Hz, 1H), 8.36 (dd, J=9, 2.1 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 4.90 (s, 2H), 3.59 (s, 3H).

Workup

  1. additionwas added
  2. customthe internal temperature below 5° C
  3. additionAfter the addition
  4. waitat RT for 2 h
  5. additionThe mixture was poured into ice cold water
  6. customCollection of the precipitated solid
  7. filtrationby filtration
  8. washwashing with cold water until the pH of the eluent

Sources & evidence

ORD record
ord-8ad67024618f46b1ac0a686e285236d3
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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