Nitric Acid → 2-Oxo-5-chloro-6-nitrobenzothiazoline

HRID 1164522Notes

Reaction equation

HRID 1164522 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:4]=2[S:3]1.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([Cl:11])[C:9]([N+:17]([O-:19])=[O:18])=[CH:10][C:4]=2[S:3]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 6038292(3H)-Benzothiazolone, 5-chloro-

Product 1

HCID 130970932-Oxo-5-chloro-6-nitrobenzothiazolineYield 93.3%

Procedure

To a mixture of 2-oxo-5-chlorobenzothiazoline (465 g) in conc.sulfuric acid (500 ml) was added dropwise a solution of nitric acid (d=1.42, 275 g) in conc.sulfuric acid (500 ml) with stirring at 10° C. during an hour. After the stirring was continued for an hour under ice-cooling, to the resultant mixture was added ice-water (10 liters) to give crystals, which were separated by filtration, washed with water and dried to give 2-oxo-5-chloro-6-nitrobenzothiazoline (539 g).

Workup

  1. waitAfter the stirring was continued for an hour under ice-
  2. customto give crystals, which
  3. customwere separated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6cb3409a161c49a4b3d77a0356b64b8e
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

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