Sodium Dithionite → HCID 11172979, compound

HRID 1991194Notes

Reaction equation

HRID 1991194 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:6]=1[S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CO.O>[NH2:11][C:10]1[C:5]([NH:4][CH2:3][CH2:2][OH:1])=[C:6]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:15])=[O:16])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 11266237HCID 11266237, compound

Product 1

HCID 11172979HCID 11172979, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[(2-hydroxyethyl)amino]-N,N-dimethyl-3-nitrobenzenesulfonamide (107 mg, 0.37 mmol) in methanol (2 mL) a solution of 85% sodium hydrosulfite (0.30 g, 1.5 mmol) in water (1.2 mL) was added. The obtained suspension was heated at 60° C. for 10 min. The volatiles were removed in vacuo, and the residue was partitioned between a saturated solution of sodium bicarbonate and ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated in vacuo affording 3-amino-2-[(2-hydroxyethyl)amino]-N,N-dimethylbenzenesulfonamide, 69 mg (72 %) as an oil: MS (ESI) m/z 260 [M+H].

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between a saturated solution of sodium bicarbonate and ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f14a201be674010b357aadc68f5ed36
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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