Dichloromethane → HCID 135626398, compound

HRID 543615Notes

Reaction equation

HRID 543615 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:17][C:18]1[C:19](Cl)=[N:20][CH:21]=[CH:22][CH:23]=1.C(Cl)Cl>C(O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:2]2[NH:1][C:19]3[N:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 128702-Amino-5-chlorobenzophenoneHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 135626398HCID 135626398, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 15.0 g (0.0647 mole) of 2-amino-5-chlorobenzophenone and 9.1 g (0.068 mole) of 3-amino-2-chloropyridine was heated at 200° C. (in an oil bath) for 0.75 hr under nitrogen atmosphere. The mixture was cooled and methylene chloride added. The mixture was stirred for 1 hr then allowed to stand overnight. Brown solid precipitate weighing 8.7 g was separated by filtration. The filtrate was evaporated under reduced pressure. The residue was combined with the brown solid and partitioned with aqueous sodium hydroxide and methylene chloride and crude product isolated as in Example 1, except the crystallizing solvent was ethanol. Recrystallization from ethanol and drying over night at 82° C./0.1 mm Hg gave 3.0 g product; m.p. 156.5°-158.5° C.

Workup

  1. temperatureThe mixture was cooled
  2. waitto stand overnight
  3. customwas separated by filtration
  4. customThe filtrate was evaporated under reduced pressure
  5. custompartitioned with aqueous sodium hydroxide and methylene chloride and crude product
  6. customisolated as in Example 1, except the crystallizing solvent
  7. customRecrystallization from ethanol
  8. customdrying over night at 82° C./0.1 mm Hg

Sources & evidence

ORD record
ord-d4fe4fb161d64becaf175ee35bec8d5b
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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