Nitric Acid → 2-(Methylsulfinyl)-6-nitrobenzo[d]thiazole

HRID 1287645Notes

Reaction equation

HRID 1287645 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][S:6][C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.S(=O)(=O)(O)[OH:17]>>[CH3:5][S:6]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:1]([O-:4])=[O:2])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 119892-(Methylthio)benzothiazole

Product 1

HCID 215057412-(Methylsulfinyl)-6-nitrobenzo[d]thiazole

Procedure

At a temperature of 0° to 15° C, a mixture of 17.6 grams of fuming nitric acid and 35 grams of concentrated sulfuric acid was added dropwise while stirring to a solution of 18.1 grams (0.1 mole) of 2-methylmercaptobenzthiazole in 70 ml of concentrated sulfuric acid. The mixture was heated to 30°-35° C and stirred for a further 3 hours at this temperature. The reaction mixture was then poured onto 200 grams of ice, the 2-methylsulfinyl-6-nitrobenzthiazole was filtered off, washed until neutral and dried. 17.5 Grams of crude product were obtained (72.4 %).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated to 30°-35° C
  3. filtrationthe 2-methylsulfinyl-6-nitrobenzthiazole was filtered off
  4. washwashed until neutral and
  5. customdried
  6. custom17.5 Grams of crude product were obtained (72.4 %)

Sources & evidence

ORD record
ord-5b5c279b9a0c4f419150c9445ccddb8a
Source dataset
uspto-grants-1976_10
Patent number
US03985762

Reaction notes

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