Methyl iodide → (RS)-3-Methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide

HRID 262120Notes

Reaction equation

HRID 262120 reaction equation
[CH3:1][I:2].[CH2:3]1[CH:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[C:5](=[S:15])[S:4]1>C(Cl)Cl>[I-:2].[CH3:1][S:15][C:5]1[S:4][CH2:3][CH:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N+:6]=12

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 21320146(RS)-9,9a-dihydrothiazolo[3,4-a]indole-3-thione

Product 1

HCID 21320148(RS)-3-Methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Methyl iodide (40 cc) is added to a solution of (RS)-9,9a-dihydrothiazolo[3,4-a]indole-3-thione (30.0 g) in methylene chloride (150 cc). After stirring for 20 hours at 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 (20 mm Hg). (RS)-3-Methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide (50.2 g), melting at 135°-140° 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 (20 mm Hg)

Sources & evidence

ORD record
ord-f7e1794c2a264129864f9e81cb2d06fb
Source dataset
uspto-grants-1979_05
Patent number
US04153699

Reaction notes

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