Hydrochloric Acid → HCID 12435002, compound

HRID 1578490Notes

Reaction equation

HRID 1578490 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[CH2:9][S:10]([CH3:12])=[O:11].Cl.[N:15]([O-])=O.[Na+]>O>[CH3:12][S:10]([C:9]1[C:8](=[O:13])[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1][N:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 143584271-(2-Aminophenyl)-2-(methylsulfinyl)ethanoneHCID 23668193Sodium Nitrite

Product 1

HCID 12435002HCID 12435002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 5.0 g (0.025 mole) of 2'-amino-2-(methylsulfinyl)-acetophenone, 30 ml (0.03 mole) of cold (15°C) 1N hydrochloric acid and 100 ml of cold water cooled to 5°C. A solution of 2.07 g (0.03 mole) of sodium nitrite in 10 ml of water was added over a period of 3 minutes with stirring, keeping the temperature at 5°C. A deep red color developed as yellow solid separated. The mixture was allowed to warm up to 20°C. After 15 minutes at 20° the product was filtered, washed with water, 2-propanol and then ether. Wt 5.0 g (64%) mp. 266°-269°. Recrystallization from N,N-dimethylformamide gave pure, white crystals melting at 274°-276°C.

Workup

  1. customat 5°C
  2. customseparated
  3. filtrationAfter 15 minutes at 20° the product was filtered
  4. washwashed with water, 2-propanol
  5. customRecrystallization from N,N-dimethylformamide
  6. customgave pure

Sources & evidence

ORD record
ord-818564f6ef65440ca56501f96f172ff0
Source dataset
uspto-grants-1976_02
Patent number
US03937704

Reaction notes

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