Triethylamine → HCID 21833453, compound

HRID 1740856Notes

Reaction equation

HRID 1740856 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[NH2:17][CH2:18][C:19]([N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[O:20].C(N(CC)CC)C>C(O)(C)C>[N+:8]([C:7]1[C:2]([NH:17][CH2:18][C:19]([N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[O:20])=[N:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127424812-amino-N,N-dipropyl-acetamideHCID 22617793HCID 22617793, compound

Product 1

HCID 21833453HCID 21833453, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-5-nitro-2-phenylpyrimidine (6.0 g), 2-amino-N,N-dipropylacetamide (6.0 g), triethylamine (5.2 g) and isopropanol (70 ml) is refluxed for six hours. The reaction mixture is concentrated under reduced pressure, and to the residue are added chloroform and water. The chloroform layer is collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from ethanol to give the desired compound (8.8 g), m.p. 142-143° C.

Workup

  1. temperatureis refluxed for six hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionto the residue are added chloroform and water
  4. customThe chloroform layer is collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1c09c96e27884cc3ab651246347fff95
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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