Hydrochloric Acid → HCID 17927799, compound

HRID 2301603Notes

Reaction equation

HRID 2301603 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([N+:22]([O-])=O)[C:16]=1[OH:25])(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([NH2:22])[C:16]=1[OH:25])(=[O:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 18373541HCID 18373541, compound

Product 1

HCID 17927799HCID 17927799, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of N-(2-benzyloxyethyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (157 mg, 0.4mmol) in THF (15 mL) and 5% aq. NaHCO3 (10 mL) was stirred at room temperature, sodium dithionite (1.5 g) was added in 0.2 g potion. The mixture was acidified with 1 N aq. HCl, extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to give the desired product (120 mg, 82%). LC-MS (m/z) 357.0 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6aae99d54e2f41abba4406b0c34ef9a6
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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