Aniline → 2-(2-Methylthioethoxy)-phenylhydrazine

HRID 4243

Reaction equation

HRID 4243 reaction equation
[NH2:1]C1C=CC=CC=1.[CH3:8][S:9][CH2:10][CH2:11][O:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].N([O-])=O.[Na+].O.O.Cl[Sn]Cl.[OH-].[Na+]>O.Cl.CCOCC.C(O)(=O)C>[CH3:8][S:9][CH2:10][CH2:11][O:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][NH2:1]

Participants

10

Reactant 5

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 542131632-(2-Methylthioethoxy)aniline

Product 1

HCID 542892902-(2-Methylthioethoxy)-phenylhydrazine

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

27.4 g of the aniline obtained under (b) are placed into 45 ml of glacial acetic acid and, with ice cooling, a mixture of 37 ml of concentrated HCl and 75 ml of H2O is added. The formed suspension is diazotised at 0°-5° C. with 10.3 g of NaNO2 in 22 ml of water. The diazonium solution is subsequently stirred at 0° C. for 10 minutes, and a solution of 80.7 g of SnCl2.2H2O in 112 ml of concentrated HCl is then quickly added with cooling. After 4 hours, water is added to the reaction mixture, and extraction is repeatedly performed with ether. The aqueous phase is afterwards rendered alkaline with a 10% aqueous sodium hydroxide solution, and extracted three times with ether. After customary further processing of the ether phases, there is obtained the compound of the formula ##STR61## having a melting point of 72.5°-74.5° C.

Workup

  1. additionis added
  2. temperaturewith cooling
  3. extractionextracted three times with ether
  4. customAfter customary further processing of the ether phases, there is obtained the compound of the formula

Sources & evidence

ORD record
ord-8ff8d568cf1248518f7da91bcabe7759
Source dataset
uspto-grants-1988_02
Patent number
US04725302

Linked notes

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