Hydrochloric Acid → N,N-dibutyl-p-nitrosoaniline

HRID 653139Notes

Reaction equation

HRID 653139 reaction equation
[N:1]([O-:3])=O.[Na+].[CH2:5]([N:9]([CH2:16][CH2:17][CH2:18][CH3:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH3:8].Cl.[OH-].[Na+]>O>[CH2:5]([N:9]([CH2:16][CH2:17][CH2:18][CH3:19])[C:10]1[CH:15]=[CH:14][C:13]([N:1]=[O:3])=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61154N,N-DibutylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 13843803N,N-dibutyl-p-nitrosoanilineYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution was prepared by dissolving 18.5 g (0.26 mol) of sodium nitrite, of a purity of 97%, in 30 ml of water. This solution was added dropwise to a solution composed of 51.3 g (0.25 mol) of N,N-dibutylaniline, 200 g of water and 105 ml of conc HCl (35 to 38%) at a temperature between 10° and 20° C. for one-half hour. After stirring the solution obtained for one hour, the solution was neutralized to pH 8 with a 15% aqueous solution of sodium hydroxide. The crystals obtained were filtered, washed sufficiently on filter paper and thereafter dried with hot-air at 50° C. for 48 hours. 28.1 g of N,N-dibutyl-p-nitrosoaniline with a melting point of 122°~124° C. was obtained. The yield was 48.0%.

Workup

  1. customA solution was prepared
  2. additionThis solution was added dropwise to a solution
  3. customobtained for one hour
  4. customThe crystals obtained
  5. filtrationwere filtered
  6. washwashed sufficiently
  7. filtrationon filter paper
  8. customdried with hot-air at 50° C. for 48 hours

Sources & evidence

ORD record
ord-306be1c229034bdfad9d557122cc45d0
Source dataset
uspto-grants-1987_06
Patent number
US04675355

Reaction notes

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