3-Methyl-2-butanone → HCID 86707260, compound

HRID 630592Notes

Reaction equation

HRID 630592 reaction equation
[NH:1]([C:3]1[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6]([C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1)N.[CH:15]([C:18]([CH3:20])=O)([CH3:17])[CH3:16]>CC(O)=O>[CH3:20][C:18]1[C:15]([CH3:17])([CH3:16])[C:4]2[C:3](=[C:8]3[CH:9]=[CH:10][S:11][C:7]3=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=2)[N:1]=1

Participants

4

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 86712482HCID 86712482, compound

Product 1

HCID 86707260HCID 86707260, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-hydrazinyl-1-benzothiophene-7-carboxylic acid CC (208 mg, 1.0 mmole) and methyl isopropyl ketone (457 mg, 5.3 mmole) in 5 mL HOAc was heated at 120° C. for 1.5 hr and cooled down to 25° C. HOAc was removed in vacuo the product was purified with CombiFlash silica gel column chromatography (eluted with CH2Cl2/MeOH stepping gradient 100:0 to 80:20). The yield of the desired product CD was 210 mg (81%).

Workup

  1. customHOAc was removed in vacuo the product
  2. customwas purified with CombiFlash silica gel column chromatography (eluted with CH2Cl2/MeOH stepping gradient 100:0 to 80:20)

Sources & evidence

ORD record
ord-278ca484ee684d2abcfb8375ea5f252c
Source dataset
uspto-grants-2016_04
Patent number
US09315864B2

Reaction notes

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