Triethylamine → HCID 67079909, compound

HRID 655544Notes

Reaction equation

HRID 655544 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=2)[NH2:10])[CH:2]=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].C(N(CC)CC)C>O1CCCC1>[C:18]1([O:17][C:15](=[O:16])[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 4595213-(Pyridin-3-yl)aniline

Product 1

HCID 67079909HCID 67079909, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-pyridin-3-ylaniline (500 mg, 2.94 mmol) in tetrahydrofuran (6 mL) was added at room temperature to a solution of phenyl chloroformate (450 mg, 2.94 mmol), then triethylamine (288 mg, 2.84 mmol) was added. After 15 min the reaction mixture was concentrated under vacuum, then the residue was partitioned between ethyl acetate and 1 M aq. sodium hydrogencarbonate solution. The organic layer was dried (MgSO4) and evaporated. The residue was taken up in tetrahydrofuran (1 mL), then heptane (10 mL) was added. The slurry was stirred for 30 min, then the precipitate was collected by filtration to afford the title compound (566 mg, 68%). Off-white solid, MS (ISP)=291.1 (M+H)+.

Workup

  1. concentrationAfter 15 min the reaction mixture was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and 1 M aq. sodium hydrogencarbonate solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. additionheptane (10 mL) was added
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-482a700840964cf99f32efb8f20bdbf3
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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