Triethylamine → 2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetonitrile

HRID 1199009Notes

Reaction equation

HRID 1199009 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:16][S:17][CH2:18][C:19]#[N:20].C(OCl)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:12][CH:13]=[CH:14][C:15]=1[CH:18]([S:17][CH3:16])[C:19]#[N:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 760802-AminobenzophenoneHCID 99295MethylthioacetonitrileHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 156347292-Amino-3-benzoyl-alpha-(methylthio)benzeneacetonitrileYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-69 °C

Procedure

To a slurry of 29.6 g (0.15 mole) of 2-aminobenzophenone and 13.1 g (0.15 mole) of (methylthio)acetonitrile in 400 ml of methylene dichloride at a temperature of -68° C. was added dropwise 16.8 g (0.155 mole) of t-butyloxychloride at a rate to ensure that the reaction temperature did not exceed -64° C. The resulting solution was stirred at -69° C. for one hour, treated with 15.7 g (0.155 mole) of triethylamine and allowed to warm to ambient temperature. The solution obtained was washed twice with water, dried over sodium sulphate, and concentrated to give 45.2 g of a dark oil as the residue. This residue was chromatographed on 1 kg of silica gel to yield 22.5 g (53%) of the title compound as tan crystals, m.p. 107°-108° C.

Workup

  1. customdid not exceed -64° C
  2. temperatureto warm to ambient temperature
  3. customThe solution obtained
  4. washwas washed twice with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-757f52ec13f7478aa92673a03609bd6a
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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