Tetrahydrofuran → 2-Amino-5-(diethylamino)toluene

HRID 459419

Reaction equation

HRID 459419 reaction equation
S(O)(O)(=O)=O.[CH2:6]([N:8]([CH2:17][CH2:18]NS(C)(=O)=O)[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:16])[CH:10]=1)[CH3:7].C(=O)([O-])[O-].[Na+].[Na+].C1COCC1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O>[CH3:7][CH2:6][N:8]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:16])[CH:10]=1)[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 62648Ammonium PersulfateHCID 13076776CD-III

Product 1

HCID 673642-Amino-5-(diethylamino)toluene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 0.73 g of the following coupler for comparison (C-2) (Compound (2) described in U.S. Pat. No. 5,455,149), 0.80 g of N-ethyl-N-(β-methanesulfonamidoethyl)-3-methyl-4-aminoaniline sulfate, 3.75 g of sodium carbonate, 60 ml of THF and 50 ml of water, a solution of 1.45 g of ammonium persulfate dissolved in 10 ml of water was gradually added with stirring at room temperature. After stirring the reaction mixture at 60° C. for 10 minutes, the THF layer was separated and purified by silica gel column chromatography, to obtain a dye for comparison (CD-2) which was a yellow azomethine dye for comparison as shown below.

Workup

  1. additionwas gradually added
  2. stirringAfter stirring the reaction mixture at 60° C. for 10 minutes
  3. customthe THF layer was separated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d93cd2236ea54e04b46899ce28a5ff0c
Source dataset
uspto-grants-2007_03
Patent number
US07193080B2

Linked notes

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