4-Toluenesulfonyl chloride → HCID 178429126, compound

HRID 1910788Notes

Reaction equation

HRID 1910788 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=S)([CH3:5])[CH3:4].[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1.O>[CH3:4][C:3]1([CH3:5])[CH2:2][O:1][C:7](=[N:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[NH:6]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 8626742HCID 8626742, compound

Product 1

HCID 178429126HCID 178429126, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(2-hydroxy-1,1-dimethyl-ethyl)-3-(4-nitro-phenyl)-thiourea (3.25 g, 12 mmol) in THF was added 0.5 M aqueous sodium hydroxide (60.4 mL, 30.2 mmol), followed by dropwise addition of a solution of p-toluenesulfonyl chloride (2.52 g, 13.2 mmol) in THF (20 mL). The mixture was stirred at r.t. for 3 h then diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give (4,4-dimethyl-oxazolidin-2-ylidene)-(4-nitro-phenyl)-amine (2.7 g, 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-551ec4304f8041fcae99c426cc290b14
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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