HCID 178463839, compound → HCID 178463838, compound

HRID 555194Notes

Reaction equation

HRID 555194 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]1[CH:9]=[CH:8][C:7](/[N:10]=[N:11]/[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2]>CO.O>[NH2:18][C:15]1[CH:14]=[CH:13][C:12](/[N:11]=[N:10]/[C:7]2[CH:8]=[CH:9][C:4]([N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 178463839HCID 178463839, compound

Product 1

HCID 178463838HCID 178463838, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

56.7 g of N,N-diethyl-4-[(E)-(4-nitrophenyl)diazenyl]aniline (0.19 M) were slurried in 270 ml of methanol at 60° C. and a solution of 147 g of sodium hydrogen sulfide-1-hydrate (1.98 M) in 150 ml of water was added cautiously. Upon addition, the former thick suspension became more liquid and the reaction mixture boiled heavily. When addition was complete, it was stirred for 0.5 h at 60° C., then cooled to room temperature and 400 ml of ice-water were added. The resulting suspension was stirred for 10 min., thereafter the solids were filtered off and washed several times with warm water, giving almost pure N-{4-[(E)-(4-aminophenyl)diazenyl]phenyl}-N,N-diethylamine as red-orange solid, used without drying in the next step.

Workup

  1. additionUpon addition
  2. additionWhen addition
  3. temperaturecooled to room temperature
  4. stirringThe resulting suspension was stirred for 10 min.
  5. filtrationthe solids were filtered off
  6. washwashed several times with warm water

Sources & evidence

ORD record
ord-78693e40c75b4a179ae029cb2e8b07e9
Source dataset
uspto-grants-2011_11
Patent number
US08053039B2

Reaction notes

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