Acetic Acid → 3-nitrodibenzothiophene S,S-dioxide

HRID 2398779Notes

Reaction equation

C(O)(=O)C.S(=O)(=O)(O)O.[CH:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15](=[O:24])(=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1.[N+:25]([O-])([OH:27])=[O:26]>O>[N+:25]([C:21]1[CH:20]=[CH:19][C:17]2[C:18]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[S:15](=[O:24])(=[O:23])[C:16]=2[CH:22]=1)([O-:27])=[O:26]

Participants

Conditions

Temperature: 4 °C

Procedure

To a mixture of acetic acid (77 ml) and sulphuric acid (77 ml) was added dibenzothiophene-5,5-dioxide (35.0 g), and the mixture cooled to 4° C. Addition of a total of 197 g. (131 ml) fuming nitric acid was begun, but in a short time the resulting paste became too thick to stir efficiently, and a further 77 ml. acetic acid was added. Local heating due to inefficient stirring was observed to occur, but the temperature of the reaction mixture was maintained at 4° C. as far as was possible. When the addition was complete (ca. 20 min.), the mixture was stirred at 4° C. for a further 30 min., and then poured into water. The crude nitrocompound was filtered off and recrystallised from dimethylformamide, m.p. 259° C.

Workup

additionAddition of a total of 197 g
temperatureLocal heating due
stirringto inefficient stirring
temperaturethe temperature of the reaction mixture was maintained at 4° C. as far
additionWhen the addition
custom(ca. 20 min.)
stirringthe mixture was stirred at 4° C. for a further 30 min.
filtrationThe crude nitrocompound was filtered off
customrecrystallised from dimethylformamide, m.p. 259° C.

Sources & evidence

ORD record: ord-6f7c09bd56d44a87b9a47cd88233d275
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04025635

Reaction notes

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