Hydrochloric Acid → HCID 86723855, compound

HRID 576756Notes

Reaction equation

HRID 576756 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[S:10][CH3:11].Cl.[N:13]([O-])=O.[Na+].[Sn](Cl)Cl>C(O)C>[NH:1]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[S:10][CH3:11])[NH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 22098582HCID 22098582, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86723855HCID 86723855, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-amino-3-(methylthio)benzonitrile (71.1 mg) and 5N aqueous hydrochloric acid (2.0 ml)/ethanol (0.5 ml) was added under ice cooling sodium nitrite (32.5 mg) and the resulting mixture was stirred for one and a half hours. To the reaction mixture was added tin(II) chloride (101.4 mg) and the resulting mixture was stirred at 0° C. for two and a half hours. The reaction mixture was filtered, and the mother liquor was basified (pH=about 10) with potassium carbonate and extracted with chloroform (30 ml) three times, and the organic layer was dried over sodium sulfate and then concentrated under reduced pressure to afford 4-hydrazinyl-3-(methylthio)benzonitrile (57.7 mg).

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for two and a half hours
  2. filtrationThe reaction mixture was filtered
  3. extractionextracted with chloroform (30 ml) three times
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1c9fad04e014082a46f18cb932dc383
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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