Toluene → (S)-3-chloro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium chloride

HRID 2420096Notes

Reaction equation

HRID 2420096 reaction equation
[C:1]([Cl:4])([Cl:3])=O.C1(C)C=CC=CC=1.[CH2:12]1[C@H:24]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH2:23]2)C(=S)[S:13]1>O1CCCC1>[Cl-:3].[Cl:4][C:1]1[S:13][CH2:12][C@@H:24]2[CH2:23][C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16][N+:15]=12

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 54272298(10aS)-1,5,10,10a-Tetrahydro-3H-[1,3]thiazolo[3,4-b]isoquinoline-3-thione

Product 1

HCID 86735297(S)-3-chloro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution (20 cc) of phosgene in toluene (containing 2 mols of phosgene per liter) is added dropwise in the absence of moisture whilst stirring and at a temperature of about 20° C to a solution of (S)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (2.2 g) in tetrahydrofuran (25 cc). The mixture becomes cloudy after 15 minutes; it is stirred for 5 hours and heated at 50° C for 1 hour. The solvents are evaporated under reduced pressure (25 mm Hg) to give (S)-3-chloro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium chloride (2.6 g) in the form of a very hygroscopic white crystalline powder.

Workup

  1. customafter 15 minutes
  2. customThe solvents are evaporated under reduced pressure (25 mm Hg)

Sources & evidence

ORD record
ord-af5300eda0bb413d8b63a25ec6dee65c
Source dataset
uspto-grants-1978_08
Patent number
US04108999

Reaction notes

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