Sulfuric Acid → HCID 22991730, compound

HRID 1168119Notes

Reaction equation

HRID 1168119 reaction equation
[CH2:1]([N:3]([CH2:12][CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH3:11])[CH3:2].[S:15](=[O:19])(=[O:18])([OH:17])[OH:16]>>[S:15]([OH:19])([OH:18])(=[O:17])=[O:16].[CH2:1]([N:3]([CH2:12][CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH3:11])[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric Acid2×HCID 423795HCID 423795, compound

Product 1

HCID 22991730HCID 22991730, compoundYield 94%

Procedure

A three-neck, 5 liter round bottom flask contained 328.0 g. of N-ethyl-N-(2-hydroxyethyl)-2-methyl-p-phenylenediamine (assay 98.0%, 1.655 moles), and was equipped with an overhead agitator, an addition funnel, and a reflux condenser. The flask was carefully purged with nitrogen to remove any residual oxygen. The flask was charged with 2,150 g of anhydrous ethyl alcohol and 32 g of water. The solution was agitated at room temperature for ten minutes. The addition funnel was charged with 96% sulfuric acid (185.4 g., 1.815 moles). The sulfuric acid was added to the free base solution over a period of 30 minutes, allowing the temperature to rise to about 45-50° C. The solution was then heated to 75° C., and held at this temperature for 30 minutes. The solution was thereafter cooled to 10° C. over a two hour period. The acid salt product, N-ethyl-N-(2-hydroxyethyl)-2-methyl-p-phenylenediamine sulfate, was formed as a white precipitate. The solids were isolated by filtration, then washed with ethyl alcohol having a temperature of about 0-20° C. The solids were dried at 60° C. and under 10 mm psia for 16 hours. The dried N-ethyl-N-(2-hydroxyethyl)-2-methyl-p-phenylenediamine sulfate, a white crystalline material, weighed 455.0 g. (1.556 moles, 94.0% yield from free base). The data for the isolation of CD-4 acid salt in three separate experiments from distilled, purified, N-ethyl-N-(2-hydroxyethyl)-2-methyl-p-phenylenediamine by the process described above are shown in Table V below.

Workup

  1. customA three-neck, 5 liter round bottom flask contained
  2. customThe flask was carefully purged with nitrogen
  3. customto remove any residual oxygen
  4. additionThe flask was charged with 2,150 g of anhydrous ethyl alcohol and 32 g of water
  5. customto rise to about 45-50° C
  6. temperatureThe solution was then heated to 75° C.
  7. temperatureThe solution was thereafter cooled to 10° C. over a two hour period

Sources & evidence

ORD record
ord-429e6c44c8a84ffb8bfc288b93542f64
Source dataset
uspto-grants-2003_09
Patent number
US06623914B2

Reaction notes

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