Acetyl chloride → HCID 54371506, compound

HRID 2396745Notes

Reaction equation

HRID 2396745 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[N:14]=[C:13]([N:15]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([NH2:30])=[C:11]([NH:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:10]=1.[C:40](Cl)(=[O:42])[CH3:41].C(OCC)(=O)C.CCCCCC>C(Cl)Cl.O>[C:40]([C:10]1[C:11]([NH:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:12]([NH2:30])[C:13]([N:15]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:14][C:9]=1[CH3:8])(=[O:42])[CH3:41]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21226206Ethyl acetate hexaneHCID 54478735HCID 54478735, compound

Product 1

HCID 54371506HCID 54371506, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (2 mL) was added to a solution of 6-methyl-N4 -(2-phenylethyl)-N2,N2 -bis(phenylmethyl)-pyridine-2,3,4-triamine (6 g, 14.2 mmole) in methylene chloride (50 mL). Acetyl chloride (1.1 mL, 15.5 mmole) was slowly added to the reaction mixture which was then heated on a steam bath for about 1 hour. The reaction mixture was stirred at ambient temperature overnight then diluted with water and methylene chloride. The organic phase was separated, washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide a light green solid. This solid was slurried with ethyl acetate/hexane then recrystallized from ethyl acetate/hexane to provide 4.1 g of a white solid. A small portion (0.8 g) was purified by silica gel column chromatography to provide the desired compound as a white solid, m.p. 152°-153° C. Analysis: Calculated for C30H32N4O: % C, 77.56; % H, 6.94; % N, 12.06; Found: % C, 77.61; % H, 6.89: % N, 12.05.

Workup

  1. temperaturewas then heated on a steam bath for about 1 hour
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto provide a light green solid
  7. customthen recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f58a4f7c9eb54a029fc00d845706baba
Source dataset
uspto-grants-1996_02
Patent number
US05494916

Reaction notes

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