Triethylamine → HCID 20199809, compound

HRID 1156065Notes

Reaction equation

HRID 1156065 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].CC[C:17](OCC)=[S:18].[C:22]([O:26]Cl)(C)(C)[CH3:23].C(N(CC)CC)C>C(Cl)Cl>[CH3:17][S:18][CH:23]1[C:3]2[C:2](=[C:7]([CH3:8])[CH:6]=[CH:5][C:4]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:1][C:22]1=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1498803-Amino-4-methylbiphenylHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetate

Product 1

HCID 20199809HCID 20199809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of 30.6 grams (0.13 mole) of 3-amino-4-methylbiphenyl in 400 milliliters of methylene chloride is cooled to -65° C. and treated with 17.0 grams (0.13 mole) of ethyl 2-methylthioacetate and then 14.2 grams (0.132 mole) of t-butylhypochlorite while maintaining the temperature below -60° C. The reaction mixture is stirred at -65° C. for 1.5 hours, treated with 13.3 grams (0.132 mole) of triethyl amine and allowed to warm to ambient temperature. The solution is washed twice with water and concentrated. The residue is dissolved in 200 milliliters of methanol, 40 milliliters of 3 N hydrochloric acid are added, and the mixture refluxed overnight. The solution is concentrated until a solid begins to precipitate. The mixture is cooled, and the solid collected by filtration.

Workup

  1. temperatureto warm to ambient temperature
  2. washThe solution is washed twice with water
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in 200 milliliters of methanol
  5. addition40 milliliters of 3 N hydrochloric acid are added
  6. temperaturethe mixture refluxed overnight
  7. concentrationThe solution is concentrated until a solid
  8. customto precipitate
  9. temperatureThe mixture is cooled
  10. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-9d08f8baefdf406987d21ebffff36f75
Source dataset
uspto-grants-1982_06
Patent number
US04333951

Reaction notes

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