Ammonium Chloride → HCID 20296004, compound

HRID 1389933Notes

Reaction equation

HRID 1389933 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH:12]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:13]([NH2:15])=[O:14].[Cl-].[NH4+]>[Fe].CC1C=CC=CC=1>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]([CH:12]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:13]([NH2:15])=[O:14])[C:4]([Cl:11])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 20296008HCID 20296008, compound

Product 1

HCID 20296004HCID 20296004, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

To a stirred and refluxed mixture of 37.5 parts of 2,6-dichloro-α-[(4-chlorophenyl)amino]-3-nitrobenzeneacetamide, 500 parts of an ammonium chloride solution 1 N and 800 parts of methylbenzene are added 28 parts of iron powder. Upon completion, stirring at reflux is continued for 50 minutes. The reaction mixture is filtered and the crystallized product is filtered off from the filtrate. It is boiled in 1000 parts of methylbenzene: one part dissolves, but crystallized again upon cooling to room temperature. It is filtered off and dried, yielding 7.1 parts of 3-amino-2,6-dichloro-α-[(4-chlorophenyl)amino]benzeneacetamide; mp. 231.8° C.

Workup

  1. temperaturerefluxed
  2. stirringUpon completion, stirring
  3. temperatureat reflux
  4. filtrationThe reaction mixture is filtered
  5. filtrationthe crystallized product is filtered off from the filtrate
  6. dissolutionone part dissolves
  7. customcrystallized again
  8. filtrationIt is filtered off
  9. customdried

Sources & evidence

ORD record
ord-81f79455352b44e3abbf0b51fc21ac18
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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