Sodium Carbonate → HCID 56617843, compound

HRID 1110800Notes

Reaction equation

HRID 1110800 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3][CH2:4][NH2:5].[CH3:22][O:23]C(OC)N(C)C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3][CH2:4][NH:5][CH:22]=[O:23]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 78373Dimethylformamide dimethyl acetalHCID 53878846HCID 53878846, compound

Product 1

HCID 56617843HCID 56617843, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 580 mg (2 mmol) of 3,7,11, 15-tetramethyl-2,6,10,14-hexadecatetraenylamine (hereinafter abbreviated as tetraprenylamine) II-1 in 20 ml of anhydrous tetrahydrofuran is added 953 mg (8 mmol) of N,N-dimethylformamide dimethylacetal. The mixture is heated under reflux for 3 hours, mixed with 15 ml of 10% aqueous sodium carbonate, and stirred at room temperature for 4 hours. The reaction mixture is concentrated, and the resulting residue is dissolved in 50 ml of CH2Cl2 and washed twice with 50 ml of water. The resulting mixture is dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue is purified by silica-gel column chromatography and eluted with AcOEt to give 410 mg of the titled compound I-1 as colorless oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture is concentrated
  4. dissolutionthe resulting residue is dissolved in 50 ml of CH2Cl2
  5. washwashed twice with 50 ml of water
  6. dry with materialThe resulting mixture is dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is purified by silica-gel column chromatography
  9. washeluted with AcOEt

Sources & evidence

ORD record
ord-96e89a31f60b46139649f1a0bea609b2
Source dataset
uspto-grants-1990_12
Patent number
US04977170

Reaction notes

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