Sodium Chloride → 3-(Isopropylsulfonyl)amino-4-aminobenzophenone

HRID 1249281Notes

Reaction equation

HRID 1249281 reaction equation
[CH:1]([S:4]([NH:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])(=[O:6])=[O:5])([CH3:3])[CH3:2].O1CCCC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl-].[Na+]>O>[CH:1]([S:4]([NH:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:21]=1[NH2:22])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 133631483-(Isopropylsulfonyl)amino-4-nitrobenzophenone

Product 1

HCID 133631493-(Isopropylsulfonyl)amino-4-aminobenzophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.91 g. (0.0112 m.) of 3-(isopropylsulfonyl)amino-4-nitrobenzophenone in 60 ml. of tetrahydrofuran (THF) was added dropwise over a period of 30 minutes to a stirred solution of 23.7 g. of sodium hydrosulfite in 200 ml. of water. After 60 minutes of additional stirring, solid sodium chloride was added and the layers were separated. The aqueous layer was extracted with THF, and the combined THF extracts were washed with a saturated solution of sodium chloride. Evaporation of the THF gave crude 3-(isopropylsulfonyl)amino-4-aminobenzophenone which was used without further purification in the subsequent cyclization. A small sample was crystallized from isopropanol several times to give the pure compound as colorless blocks, m.p. about 143°-145° C.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with THF
  3. washthe combined THF extracts were washed with a saturated solution of sodium chloride
  4. customEvaporation of the THF

Sources & evidence

ORD record
ord-1a625a9683de475a9b49fa7d36d59eb2
Source dataset
uspto-grants-1986_12
Patent number
US04629811

Reaction notes

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