Methyl iodide → (S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

HRID 262108Notes

Reaction equation

HRID 262108 reaction equation
[CH2:1]1[C@H:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[C:3](=[S:14])[S:2]1.[CH3:15][I:16]>>[I-:16].[CH3:15][S:14][C:3]1[S:2][CH2:1][C@@H:13]2[CH2:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH2:5][N+:4]=12

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 54272298(10aS)-1,5,10,10a-Tetrahydro-3H-[1,3]thiazolo[3,4-b]isoquinoline-3-thione

Product 1

HCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Procedure

(S)-1,5,10,10a-Tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (38 g) is dissolved in methyl iodide (500 cc). After 15 hours at a temperature of about 20° C., the resulting crystals are filtered off, washed with diethyl ether (2×50 cc) and then dried at 20° C. under reduced pressure (1 mm Hg). (S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (61.5 g), which melts at 140°-150° C. with decomposition, is thus obtained.

Workup

  1. filtrationthe resulting crystals are filtered off
  2. washwashed with diethyl ether (2×50 cc)
  3. customdried at 20° C. under reduced pressure (1 mm Hg)

Sources & evidence

ORD record
ord-eb40d7a998024836aa3f4383230c7052
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

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