Ethanol → HCID 59354856, compound

HRID 1776348Notes

Reaction equation

HRID 1776348 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10](=[O:17])[C:11]#[C:12][C:13](O)([CH3:15])[CH3:14])[CH:7]=[CH:6][C:5]=12.C(NCC)C.C([OH:25])C>>[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]3[O:17][C:13]([CH3:14])([CH3:15])[C:12](=[O:25])[CH:11]=3)[CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 59354857HCID 59354857, compound

Product 1

HCID 59354856HCID 59354856, compoundYield 83%

Procedure

To a stirred solution of 1-(benzo[c][1,2,5]thiadiazol-5-yl)-4 -hydroxy-4-methylpent-2-yn-1-one (0.6 g, 2.597 mmol) in ethanol (10 mL), a solution of diethyl amine (0.189 g, 2.597 mmol) in EtOH (5 mL) was added dropwise at RT. The reaction mixture was then stirred for additional 3 h. The ethanol was then removed, and the mixture further diluted with EtOAc (10 mL). The combined organic layers were washed with water (5 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford 5-(benzo[c][1,2,5]thiadiazol-5-yl)-2,2-dimethylfuran-3(2H)-one (0.5 g, 83%) as a light yellow solid.

Workup

  1. customThe ethanol was then removed
  2. additionthe mixture further diluted with EtOAc (10 mL)
  3. washThe combined organic layers were washed with water (5 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6551a0a8ea644736ac3fbe07cf92a10d
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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