Triethylamine → HCID 22054125, compound

HRID 1830445Notes

Reaction equation

HRID 1830445 reaction equation
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:25][C:26]1[C:31](=[O:32])[C:30]([CH3:33])=[C:29]([CH3:34])[C:28](=[O:35])[C:27]=1[CH2:36][C:37]1[CH:38]=[CH:39][C:40]([O:46][C:47](=[O:49])[CH3:48])=[C:41]([CH:45]=1)[C:42](O)=[O:43]>C(Cl)Cl>[Cl:8][C:3]1[C:2]([NH:1][C:42](=[O:43])[C:41]2[CH:45]=[C:37]([CH2:36][C:27]3[C:28](=[O:35])[C:29]([CH3:34])=[C:30]([CH3:33])[C:31](=[O:32])[C:26]=3[CH3:25])[CH:38]=[CH:39][C:40]=2[O:46][C:47](=[O:49])[CH3:48])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 805282-Chloro-3-pyridylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054145HCID 22054145, compound

Product 1

HCID 22054125HCID 22054125, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-chloropyridine (0.141 g, 1.096 mmol), triethylamine (0.111 g, 1.096 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.185 g, 1.096 mmol) were added to a methylene chloride solution (100 ml) of 5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.250 g, 0.730 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) and then recrystallized from a mixed solvent of ethyl acetate and hexane (2:1) to obtain the titled compound (0.149 g, 0.329 mmol, 45%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)
  6. customrecrystallized from a mixed solvent of ethyl acetate and hexane (2:1)

Sources & evidence

ORD record
ord-e1b0aad9904949f6bd583b5af030d86d
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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