Water → HCID 54329643, compound

HRID 1195758Notes

Reaction equation

HRID 1195758 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.[CH3:22]C(C)([O-])C.[K+].CI.O>O1CCCC1>[CH3:22][N: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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 53824737HCID 53824737, compound

Product 1

HCID 54329643HCID 54329643, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl [(9-amino-1,2,3,4-tetrahydroacridin-1-yl)thio]acetate (5.06 g) in tetrahydrofuran (100 ml) was added potassium t-butoxide (2.3 g). The mixture was stirred for 30 mins and methyl iodide (1.6 ml) was added. Stirring was continued for 2 hrs, and the reaction mixture was poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic extracts were purified by flash chromatography (ethyl acetate/dichloromethane) to give 3.42 g (72%) of the 1,3,4a,5,6,7-hexahydro-1-methyl-2H-quino-[4,3,2-ef][1,4]benzthiazepin-2-one, mp 241°-245° C. (dec.).

Workup

  1. stirringStirring
  2. waitwas continued for 2 hrs
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. customThe combined organic extracts were purified by flash chromatography (ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-b119f9f578244c04852154f3245662da
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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