Sodium Dithionite → HCID 22495874, compound

HRID 1249699Notes

Reaction equation

HRID 1249699 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:26]([O-])=O)=[C:6]([CH:25]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)=[O:8].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.CO.O>[NH2:26][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:25][C:6]=1[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)(=[O:18])=[O:17])=[CH:14][CH:15]=1)=[O:8]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 22495826HCID 22495826, compound

Product 1

HCID 22495874HCID 22495874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

11.10 g (26. 1 mmol) of 5-chloro-N-(4-(morpholine-4-sulfonyl)-phenyl)-2-nitro-benzamide were dissolved in 440 ml of tetrahydrofuran/methanol (1:1) and a solution of 27.23 g (156.4 mmol) of sodium dithionite in 330 ml of water was added dropwise. After stirring for 1 h at room temperature the organic solvents were removed in rotary evaporator, and the precipitated product was filtered off with suction and purified by chromatography over silica with methylene chloride/methanol (9:1). 5.68 g (55%) of the title compound having a melting point of 229-231° C. were obtained.

Workup

  1. customwere removed in rotary evaporator
  2. filtrationthe precipitated product was filtered off with suction
  3. custompurified by chromatography over silica with methylene chloride/methanol (9:1)
  4. customwere obtained

Sources & evidence

ORD record
ord-68835cb8c67d47278fec312913b82884
Source dataset
uspto-grants-2002_01
Patent number
US06335334B1

Reaction notes

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