Methyl iodide → (S)-3-Methylthio-7-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

HRID 461821Notes

Reaction equation

HRID 461821 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@H:9]3[CH2:16][S:15][C:14](=[S:17])[N:10]3[CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].[CH3:18][I:19]>>[I-:19].[CH3:18][S:17][C:14]1[S:15][CH2:16][C@@H:9]2[CH2:8][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]=3[CH2:11][N+:10]=12

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 54361302(S)-7-Nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thione

Product 1

HCID 86735299(S)-3-Methylthio-7-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Procedure

(S)-7-Nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (16 g.) is dissolved in methyl iodide (800 cc.). After 15 hours at a temperature of about 20° C., the crystals which have appeared are filtered off, washed with diethyl ether (2 × 30 cc.) and then dried at 20° C., under reduced pressure (1 mm.Hg). (S)-3-Methylthio-7-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (23.3 g.) is thus obtained.

Workup

  1. filtrationthe crystals which have appeared are filtered off
  2. washwashed with diethyl ether (2 × 30 cc.)
  3. customdried at 20° C., under reduced pressure (1 mm.Hg)

Sources & evidence

ORD record
ord-6d960ecfd8b64a32999009812b8ebc68
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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