3-(n-Octyloxy)-4-(p-toluenesulfonyl)aminoaniline → 3-(n-Octyloxy)-4-(p-toluenesulfonyl)aminobenzenediazonium hexafluorophosphate

HRID 248795Notes

Reaction equation

HRID 248795 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N:28]([O-])=O.[Na+].[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[K+]>CO.Cl.O>[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([N+:13]#[N:28])[CH:14]=[CH:15][C:16]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:19])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 3

HCID 197621433-(n-Octyloxy)-4-(p-toluenesulfonyl)aminoanilineHCID 23668193Sodium NitriteHCID 23688904Potassium hexafluorophosphate

Product 1

HCID 197621383-(n-Octyloxy)-4-(p-toluenesulfonyl)aminobenzenediazonium hexafluorophosphateYield 88.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Then, 39 g of 3-(n-octyloxy)-4-(p-toluenesulfonyl)aminoaniline was dissolved in a mixed solution of 300 ml of methanol and 25.3 ml of concentrated hydrochloric acid. The solution was cooled to -10° to -5° C., and a solution of 6.9 g of sodium nitrite in 14 ml of water was added thereto in several seconds and, after 10 minutes, 18.5 g of powdery potassium hexafluorophosphate was added thereto. Thereafter, 150 ml of water was dropwise added thereto over about 30 minutes, and the resulting mixture was stirred for about one hour while keeping the internal temperature at about 5° C. 3-(n-Octyloxy)-4-(p-toluene-sulfonyl)aminobenzenediazonium hexafluorophosphate precipitated as crystals was filtered out, and washed with a mixed solvent of methanol-water to obtain 48.4 g of 3-(n-octyloxy)-4-(p-toluenesulfonyl)aminobenzenediazonium hexafluorophosphate.

Workup

  1. temperatureThe solution was cooled to -10° to -5° C.
  2. waitin several seconds
  3. waitover about 30 minutes
  4. customat about 5° C
  5. custom3-(n-Octyloxy)-4-(p-toluene-sulfonyl)aminobenzenediazonium hexafluorophosphate precipitated as crystals
  6. filtrationwas filtered out
  7. washwashed with a mixed solvent of methanol-water

Sources & evidence

ORD record
ord-d7f2e8a791ff4a58a4c479771fadd5dc
Source dataset
uspto-grants-1993_05
Patent number
US05212042

Reaction notes

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