Potassium tert-butoxide → HCID 54147898, compound

HRID 1195756Notes

Reaction equation

HRID 1195756 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([S:16][CH2:17][C:18]([O:20]C)=O)[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CC(C)([O-])C.[K+]>O1CCCC1>[NH:1]1[C:2]2=[C:3]3[C:8](=[N:9][C:10]4[CH2:11][CH2:12][CH2:13][CH:14]([C:15]=42)[S:16][CH2:17][C:18]1=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4]3

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 53824737HCID 53824737, compound

Product 1

HCID 54147898HCID 54147898, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [(9-amino-1,2,3,4-tetrahydroacridin-1-yl)thio]acetate (10.3 g) in tetrahydrofuran (150 ml) was added potassium t-butoxide (4.6 g). The reaction mixture was stirred at ambient temperature for 45 mins and then concentrated. The residue was stirred in water, the solid was collected, and dried. The solid was purified by flash chromatography (ethyl acetate/dichloromethane→5% methanol/dichloromethane) to give 4.1 g (44%) of product, mp 223°-226° C. (dec.). Recrystallization from methanol gave the analytical sample, mp 223.5°-226° C. (dec.).

Workup

  1. concentrationconcentrated
  2. stirringThe residue was stirred in water
  3. customthe solid was collected
  4. customdried
  5. customThe solid was purified by flash chromatography (ethyl acetate/dichloromethane→5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5f064fda65f94e36811c2a1239cf4774
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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