Acetone → 1-(hydroxymethyl)-4-(methylthio)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinolinium iodide

HRID 364616Notes

Reaction equation

HRID 364616 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[C:6](=[S:21])[O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3.[CH3:22]C(C)=O.C[I:27]>>[I-:27].[OH:1][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N+:7]2=[C:6]([S:21][CH3:22])[O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3

Participants

4

Reactant 3

HCID 180AcetoneHCID 6328Methyl iodideHCID 148340121-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thione

Product 1

HCID 148340131-(hydroxymethyl)-4-(methylthio)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinolinium iodideYield 70%

Procedure

To a solution of 3.09 g (0.01 mole) of 1-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thione in acetone 1.94 g (0.02 mole) of methyl iodide are added. The reaction mixture is allowed to stand at room temperature for 24 hours. The crystalline product is filtered off, washed and recrystallized from a mixture of acetone and ether. Yield: 70% (decomposition).

Workup

  1. filtrationThe crystalline product is filtered off
  2. washwashed
  3. customrecrystallized from a mixture of acetone and ether

Sources & evidence

ORD record
ord-957e80f81b42439d83d5a97390616da7
Source dataset
uspto-grants-1986_08
Patent number
US04605653

Reaction notes

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