Dichloromethane → HCID 13560178, compound

HRID 637828Notes

Reaction equation

HRID 637828 reaction equation
N#N.CN(C)CCC[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]=1[NH2:21].[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26]C)C.[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34].[CH2:40](Cl)Cl>>[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH:21][C:9]1[C:10]([N:14]([CH2:40][CH2:29][CH2:28][N:25]([CH3:23])[CH3:26])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:11][CH:12]=[CH:13][CH:8]=1)=[O:34]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 86740554HCID 86740554, compound

Product 1

HCID 13560178HCID 13560178, compoundYield 74%

Procedure

To a stirred solution of 9 g (0.033 mole) of N2 -[3-(dimethylamino)propyl]-N2 -phenyl-2,3-pyridinediamine and 3.9 g (0.038 mole) triethylamine in 75 ml of dry methylene chloride was added dropwise with stirring at 15°-20° C., 6.4 g (0.037 mole) of 2-chlorobenzoyl chloride. After stirring overnight, the reaction mixture was washed with water. The methylene chloride layer was extracted twice with dilute sodium hydroxide solution, washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was triturated in isopropyl ether to give 10 g (74%) of solid. A portion of this solid was recrystallized from isopropyl alcohol-isopropyl ether to give a cream colored solid, m.p. 90°-92° C.

Workup

  1. stirringAfter stirring overnight
  2. washthe reaction mixture was washed with water
  3. extractionThe methylene chloride layer was extracted twice with dilute sodium hydroxide solution
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in isopropyl ether

Sources & evidence

ORD record
ord-d74acf394c104f1fb3e08e99e7171ced
Source dataset
uspto-grants-1985_12
Patent number
US04558132

Reaction notes

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