Ammonium Chloride → HCID 21483149, compound

HRID 1415584Notes

Reaction equation

HRID 1415584 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11](=[C:14]1[CH:19]=[C:18]([CH3:20])[C:17](=[N:21]O)[CH:16]=[C:15]1[Cl:23])[C:12]#[N:13]>[Fe].CC1C=CC=CC=1>[ClH:3].[NH2:21][C:17]1[C:18]([CH3:20])=[CH:19][C:14]([CH:11]([C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])[C:12]#[N:13])=[C:15]([Cl:23])[CH:16]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86734451HCID 86734451, compound

Product 1

HCID 21483149HCID 21483149, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

370 parts of ammonium chloride solution 0.78N are stirred and heated to reflux. Then there are added 37 parts of iron-powder, followed by the dropwise addition of a solution of 37 parts of 2,4-dichloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexandien-1-ylidene]benzeneacetonitrile in 333 parts of methylbenzene. Upon completion, stirring at reflux is continued overnight. The reaction mixture is cooled to 60° C, filtered and the filter-cake is washed with tetrahydrofuran. The filtrate is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2,2'-oxybispropane and 2-propanol, yielding 4-amino-2-chloro-α-(2,4-dichlorophenyl)-5-methylbenzeneacetonitrile hydrochloride.

Workup

  1. temperatureheated to reflux
  2. temperatureat reflux
  3. filtrationfiltered
  4. washthe filter-cake is washed with tetrahydrofuran
  5. customThe filtrate is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2fd5fa3d70ec4fde9b20eac0c74886c0
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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