Hydrochloric Acid → HCID 178450255, compound

HRID 1801480Notes

Reaction equation

HRID 1801480 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:5][C:4]=1[NH2:16])#[N:2].Cl.[N:18]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O.C(O)C>[C:28]1([N:27]=[N:18][NH:16][C:4]2[CH:5]=[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:7]([O:9][CH3:10])=[CH:8][C:3]=2[C:1]#[N:2])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 517045Sodium Acetate2×HCID 23668193Sodium NitriteHCID 583678162-Cyano-4-methoxy-5-n-butoxy phenylamine

Product 1

HCID 178450255HCID 178450255, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

0.22 g (1 mmol) 2-cyano-4-methoxy-5-n-butoxyphenylamine and 3 mL (10 mol/L) hydrochloric acid were added into a round bottom flask. The solution was cooled to 0° C. and diazotized with sodium nitrite (0.072 g, 1 mmol) dissolved in water (1.0 mL), which was added dropwise to the solution. The mixture was stirred to react for 20 min. After adjusting the pH to 5˜6 with sodium acetate, the ethanol solution of aniline (0.093 g, 1 mmol) was added dropwise to the reaction mixture to react for 2 h under stirring, while maintaining the reaction temperature at between 0˜5° C., and using sodium acetate to keep the pH value at 5-6. The solution was kept overnight, filtered, and washed with water till colorless. The crude product was purified on a silica gel column with petroleum ether:ethyl acetate (v/v)=15:1 to yield 0.154 g of orange-yellow solid crystal product with a recovery rate of 47.5%.

Workup

  1. additionwhich was added dropwise to the solution
  2. customto react for 20 min
  3. customto react for 2 h
  4. stirringunder stirring
  5. temperaturewhile maintaining the reaction temperature at between 0˜5° C.
  6. filtrationfiltered
  7. washwashed with water till colorless
  8. customThe crude product was purified on a silica gel column with petroleum ether

Sources & evidence

ORD record
ord-5e12d0e9275f476a8a23e2716ffcee07
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

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