Ammonia → 4-acetamido-2'-methyl-4'-[N,N-bis(beta-hydroxyethyl)amino]phenylazobenzene

HRID 476811Notes

Reaction equation

HRID 476811 reaction equation
[C:1]([NH:4][C:5]1[CH:11]=[CH:10][C:8](N)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.N([O-])=O.[Na+].[CH3:17][C:18]1[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=1)[N:21]([CH2:25][CH2:26][OH:27])[CH2:22][CH2:23][OH:24].[NH3:31]>O>[C:1]([NH:4][C:5]1[CH:11]=[CH:10][C:8]([C:19]2[C:18]([CH3:17])=[C:30]([N:31]=[N:4][C:5]3[CH:11]=[CH:10][CH:8]=[CH:7][CH:6]=3)[CH:29]=[CH:28][C:20]=2[N:21]([CH2:25][CH2:26][OH:27])[CH2:22][CH2:23][OH:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 70732,2'-((3-Methylphenyl)imino)bisethanolHCID 312304-AminoacetanilideHCID 23668193Sodium Nitrite

Product 1

HCID 867435634-acetamido-2'-methyl-4'-[N,N-bis(beta-hydroxyethyl)amino]phenylazobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

0.2 mol (30 g) of p-acetamidoaniline, followed by 34 ml of concentrated hydrochloric acid, are added to 100 ml of water containing 300 g of crushed ice. A solution of 15.2 g of sodium nitrite in 30 ml of water is added to the suspension. The solution obtained in this way is added, after being filtered, to an ice-cold solution of 0.2 mol (39 g) of 3-methyl-N,N-bis(β-hydroxyethyl)aniline in 160 g of water containing 34 ml of concentrated hydrochloric acid. After 30 minutes stirring and making alkaline with a 20% ammonia solution, the product is obtained in the form of crystals.

Workup

  1. customThe solution obtained in this way
  2. additionis added
  3. customthe product is obtained in the form of crystals

Sources & evidence

ORD record
ord-cbdbf7b4de6d4ac89f0a8d4622545999
Source dataset
uspto-grants-1989_12
Patent number
US04886517

Reaction notes

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