Hydrochloric Acid → 3-(Isopropylsulfonyl)amino-4-nitrobenzophenone

HRID 1979972Notes

Reaction equation

HRID 1979972 reaction equation
[H-].[Na+].[CH:3]([S:6]([NH2:9])(=[O:8])=[O:7])([CH3:5])[CH3:4].F[C:11]1[CH:12]=[C:13]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].Cl>CS(C)=O>[CH:3]([S:6]([NH:9][C:11]1[CH:12]=[C:13]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])(=[O:8])=[O:7])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 3549191Propane-2-sulfonamideHCID 13363147(3-Fluoro-4-nitrophenyl)(phenyl)methanone

Product 1

HCID 133631483-(Isopropylsulfonyl)amino-4-nitrobenzophenoneYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 50 ml. of dimethylsulfoxide (DMSO) was added 1.01 g. (0.021 m.) of 50% sodium hydride in oil. After the initial gas evolution ceased, 2.53 g. (0.0206 m.) of isopropylsulfonamide [prepared according to Duguet, Rec. Trav. Chim., 25, 215 (1906)] was added. The mixture was stirred under a calcium chloride drying tube for ten minutes after which time 4.90 g. (0.020 m.) of 3-fluoro-4-nitrobenzophenone was added, followed by 20 ml. of DMSO. After stirring for five hours at room temperature, the reaction solution was poured into a mixture of ice and 1N hydrochloric acid which was then extracted several times with ethyl acetate. The extracts were combined, washed with water, and dried over magnesium sulfate. The oil remaining after evaporation was triturated with isopropanol to give 6.65 g. (95% yield) of 3-(isopropylsulfonyl)amino-4-nitrobenzophenone as a yellow powder. Crystallization from isopropanol gave pale yellow needles, m.p. about 115°-116° C.

Workup

  1. stirringAfter stirring for five hours at room temperature
  2. extractionwas then extracted several times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customafter evaporation
  6. customwas triturated with isopropanol
  7. customto give 6.65 g

Sources & evidence

ORD record
ord-7faa5467792b4d498191252ec7a1279d
Source dataset
uspto-grants-1984_11
Patent number
US04483986

Reaction notes

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