(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide → (S)-3-[(3-Butylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline

HRID 262113Notes

Reaction equation

HRID 262113 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH2:28][CH2:29][CH2:30][CH3:31])[N:22]=[CH:23]2>N1C=CC=CC=1>[CH2:28]([C:21]1[N:22]=[CH:23][C:24]2[C:19]([CH:20]=1)=[C:18]([N:17]=[C:4]1[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]1)[CH:27]=[CH:26][CH:25]=2)[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodideHCID 213201405-Amino-3-butylisoquinoline

Product 1

HCID 22807718(S)-3-[(3-Butylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinolineYield 54.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo-[3,4-b]isoquinolinium iodide (5.25 g) is added to a solution of 5-amino-3-butylisoquinoline (3 g) in pyridine (100 cc). The suspension obtained dissolves gradually. After 4 days at a temperature of about 20° C., the mixture is concentrated to dryness under reduced pressure (25 mm Hg) at 50° C. The residue is dissolved in chloroform (200 cc). This solution is washed with N aqueous sodium hydroxide solution (3×100 cc) and then with water (2×50 cc), dried over sodium sulphate, filtered and the filtrate is then concentrated to dryness under reduced pressure (40 mm Hg) at 40° C. The residue obtained is recrystallised from diisopropyl ether (50 cc). (S)-3-[(3-Butylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (3.05 g), which melts at 82° C., is thus obtained.

Workup

  1. customThe suspension obtained
  2. dissolutiondissolves gradually
  3. concentrationthe mixture is concentrated to dryness under reduced pressure (25 mm Hg) at 50° C
  4. dissolutionThe residue is dissolved in chloroform (200 cc)
  5. washThis solution is washed with N aqueous sodium hydroxide solution (3×100 cc)
  6. dry with materialwith water (2×50 cc), dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate is then concentrated to dryness under reduced pressure (40 mm Hg) at 40° C
  9. customThe residue obtained
  10. customis recrystallised from diisopropyl ether (50 cc)

Sources & evidence

ORD record
ord-0e31676c1aec473f8a95036fcb9bf755
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

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