Ammonia → 4-Methyl-5-nitrosaccharin

HRID 343747

Reaction equation

HRID 343747 reaction equation
[NH3:1].O.C[O:4][C:5]([C:7]1[C:12]([CH3:13])=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:9][C:8]=1[S:17](Cl)(=[O:19])=[O:18])=O>O1CCCC1>[CH3:13][C:12]1[C:7]2[C:5](=[O:4])[NH:1][S:17](=[O:19])(=[O:18])[C:8]=2[CH:9]=[CH:10][C:11]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 153345332-Methoxycarbonyl-3-methyl-4-nitrobenzenesulfonyl chloride

Product 1

HCID 153345344-Methyl-5-nitrosaccharin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

104 ml of 25 percent ammonia solution are initially taken, 100 ml of water are added and a solution of 48.7 g (0.166 mol) of 2-methoxycarbonyl-3-methyl-4-nitrobenzenesulfonyl chloride in 70 ml of tetrahydrofuran is then added dropwise at 10° C. After stirring at 25° C. for three hours, the mixture is concentrated on a rotary evaporator in order to remove water and THF. The residue which remains is stirred with ethyl acetate, filtered off with suction and washed with ethyl acetate. After drying under reduced pressure, 34 g (0.131 mol)=79% of theory of a white solid of m.p.: 312° C. (dec.) are obtained.

Workup

  1. concentrationthe mixture is concentrated on a rotary evaporator in order
  2. customto remove water and THF
  3. stirringThe residue which remains is stirred with ethyl acetate
  4. filtrationfiltered off with suction
  5. washwashed with ethyl acetate
  6. customAfter drying under reduced pressure, 34 g (0.131 mol)=79% of theory of a white solid of m.p.: 312° C. (dec.)
  7. customare obtained

Sources & evidence

ORD record
ord-d02c6f1f8d424c4e9f033f20fc8fce25
Source dataset
uspto-grants-1999_01
Patent number
US05863864

Linked notes

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