2-Amino-4'-chlorobenzophenone → 2-Amino-3-(4-chlorobenzoyl)-alpha-(methylthio)benzeneacetonitrile

HRID 1199010Notes

Reaction equation

HRID 1199010 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[CH:4][CH:3]=1.[CH3:17][S:18][CH2:19][C:20]#[N:21].C(OCl)(C)(C)C>C(Cl)Cl>[NH2:15][C:10]1[C:9]([C:8](=[O:16])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[CH:19]([S:18][CH3:17])[C:20]#[N:21]

Participants

5

Reactant 3

HCID 761662-Amino-4'-chlorobenzophenoneHCID 99295MethylthioacetonitrileHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 156347302-Amino-3-(4-chlorobenzoyl)-alpha-(methylthio)benzeneacetonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 46.3 g (0.2 mole) of 4'-chloro-2-aminobenzophenone and 17.4 g (0.2 mole) of methylthioacetonitrile in 1 liter of methylene dichloride at a temperature of -70° C. was added dropwise 22.2 g (0.21 mole) of tert. butyloxychloride at a rate to ensure that the reaction temperature did not exceed -65° C. The resulting solution was allowed to warm to ambient temperature, washed twice with water, dried over sodium sulphate, and concentrated to give a gum residue. The gum crystallized when it was triturated with diethyl ether. The solid was collected by filtration and recrystallized from 2-propanol to yield 43.0 g (68%) of the title compound as a tan solid, m.p. 122° C.

Workup

  1. customdid not exceed -65° C
  2. washwashed twice with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customto give a gum residue
  6. customThe gum crystallized when it
  7. customwas triturated with diethyl ether
  8. filtrationThe solid was collected by filtration
  9. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-f7d709ab2e8f43c7bfcb0d3aa454a01a
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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