Ammonium Hydroxide → 4'-[(6-Hydroxyhexyl)methylamino]-4-methylsulfonylazobenzene

HRID 1199289Notes

Reaction equation

HRID 1199289 reaction equation
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].N([O-])=O.[Na+].[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+].[OH-].[NH4+:37]>Cl.O>[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:30])[C:24]1[CH:25]=[CH:26][C:27]([N:37]=[N:9][C:8]2[CH:10]=[CH:11][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 14923Ammonium HydroxideHCID 796174-(Methylsulfonyl)anilineHCID 517045Sodium AcetateHCID 152539786-[Methyl(phenyl)amino]hexan-1-OLHCID 23668193Sodium Nitrite

Product 1

HCID 190200674'-[(6-Hydroxyhexyl)methylamino]-4-methylsulfonylazobenzeneYield 47%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A stirred suspension of 150 g (0.88 mol) of 4-methylsulfonylaniline in 1 liter of 20% hydrochloric acid at 0°-3° C. was treated dropwise with a solution of 66.5 g (0.96 mol) of sodium nitrite in 200 mL of water. N-(6-Hydroxyhexyl)-N-methylaniline (Example 1, 218 g, 1.05 mol) was added slowly, maintaining the temperature below 5° C., and the mixture was stirred for 1 hour. Sodium acetate (119 g, 0.88 mol) was added and stirring was continued for 3 hours. Concentrated ammonium hydroxide (250 mL) was added, and the mixture was stirred for 64 hours. The precipitated product was recrystallized successively from ethanol, from toluene, and then from toluene/isopropanol to produce 160 g (47%) of a red solid, mp 114°-116° C.

Workup

  1. temperaturemaintaining the temperature below 5° C.
  2. stirringstirring
  3. waitwas continued for 3 hours
  4. stirringthe mixture was stirred for 64 hours
  5. customThe precipitated product was recrystallized successively from ethanol, from toluene

Sources & evidence

ORD record
ord-037714c79f0341b288498a7a18c23c0f
Source dataset
uspto-grants-1990_02
Patent number
US04900127

Reaction notes

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