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

HRID 461806Notes

Reaction equation

HRID 461806 reaction equation
[C:1]([Cl:4])([Cl:3])=O.[CH2:5]1[C@H:17]2[N:8]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:16]2)C(=S)[S:6]1>C1(C)C=CC=CC=1.O1CCCC1>[Cl-:3].[Cl:4][C:1]1[S:6][CH2:5][C@@H:17]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12

Participants

5

Reactant 2

HCID 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 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution (20 cc.) containing 2 mols per liter of phosgene in toluene, 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 then heated to 50° C. for 1 hour. The solvents are evaporated under reduced pressure (25 mm. Hg ) at 60° C. 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. additionis added dropwise, in the absence of moisture
  2. customafter 15 minutes
  3. stirringit is stirred for 5 hours
  4. temperatureheated to 50° C. for 1 hour
  5. customThe solvents are evaporated under reduced pressure (25 mm. Hg ) at 60° C.

Sources & evidence

ORD record
ord-4ea9677059084024a1448b4fb6dfcafa
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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