Acetyl chloride → HCID 54371506, compound

HRID 263720Notes

Reaction equation

HRID 263720 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-a885bbc18e5444ccaea820093de3b058
Source dataset
uspto-grants-1997_07
Patent number
US05644063

Reaction notes

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