N-Phenyl-o-phenylenediamine → HCID 20251875, compound

HRID 1284480Notes

Reaction equation

HRID 1284480 reaction equation
[NH:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>ClCCl.N1C=CC=CC=1>[Cl:15][CH2:16][CH2:17][CH2:18][C:19]([NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:20]

Participants

5

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 20251875HCID 20251875, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-anilinoaniline (4.0 g) in a mixture of dichloromethane (20 ml) and pyridine (6.87 g) was dropwise added 4-chlorobutyryl chloride (4.29 g) at 8° C. during a period of 16 minutes. The mixture was stirred at the same temperature for 40 minutes and then diluted with ice-water. The mixture was extracted twice with dichloromethane. The combined extract was washed with 1 N hydrochloric acid and water in turn and dried over magnesium sulfate. The solvent was removed under reduced pressure to give a crystalline residue of 4-chloro-N-(2-anilinophenyl)butyramide (4.3 g).

Workup

  1. customat 8° C.
  2. customof 16 minutes
  3. extractionThe mixture was extracted twice with dichloromethane
  4. extractionThe combined extract
  5. washwas washed with 1 N hydrochloric acid and water in turn
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-32b1aac7de8c496a95dc752c60c6ea5c
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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