Triethylamine → HCID 67041495, compound

HRID 606125Notes

Reaction equation

HRID 606125 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH2:25][C:26](Cl)=[N:27][OH:28]>C(Cl)(Cl)Cl>[CH2:3]([C:2]1[O:28][N:27]=[C:26]([CH2:25][N:16]2[C:15](=[O:14])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:24])[CH:1]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127321-HexyneHCID 86616900HCID 86616900, compound

Product 1

HCID 67041495HCID 67041495, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Hexyne (5.16 g, 62.9 mmol) and triethylamine (6.36 g, 62.9 mmol) were sequentially added to a suspension of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-hydroxyethanimidoyl chloride (5.0 g, 21 mmol) in chloroform (80 mL). The solution was stirred overnight at room temperature, washed sequentially with 0.5 M hydrochloric acid and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with 3:1 to 1:1 hexane:ethyl acetate) to provide 2.14 g of 2-[(5-butylisoxazol-3-yl)methyl]-1H-isoindole-1,3(2H)-dione as a white, crystalline solid.

Workup

  1. washwashed sequentially with 0.5 M hydrochloric acid and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography on silica gel (eluting with 3:1 to 1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-341b878c575d49b7b726ca55d32d8023
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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