Thiomorpholine → 1-Thiomorpholino-3-chloro-isoquinoline

HRID 1283580Notes

Reaction equation

HRID 1283580 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.[NH:13]1[CH2:18][CH2:17][S:16][CH2:15][CH2:14]1>O1CCOCC1>[S:16]1[CH2:17][CH2:18][N:13]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([Cl:12])[N:3]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 2986251,3-Dichloroisoquinoline

Product 1

HCID 215184891-Thiomorpholino-3-chloro-isoquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 19.8 gm (0.1 mol) of 1,3-dichloro-isoquinoline [prepared according to S. Gabriel, Berichte 19, 1655 (1886)], 25.8 gm (0.25 mol) of thiomorpholine and 100 ml of dry dioxane was refluxed for 7 hours. Thereafter, the precipitated thiomorpholine hydrochloride was suction-filtered off, the filtrate was evaporated and water was added to the residue. The reaction product was suction-filtered off, dried and recrystallized from ethyl acetate, yielding 18.4 gm (69.5% of theory) of the desired compound, m.p. 133°C. In analogous manner 1-(1-oxido-thiomorpholino)-3-chloro-isoquinoline, m.p. 167°-168°C (from ethyl acetate), was prepared from 1,3-dichloro-isoquinoline and 1-oxido-thiomorpholine.

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThereafter, the precipitated thiomorpholine hydrochloride was suction-filtered off
  3. customthe filtrate was evaporated
  4. additionwater was added to the residue
  5. filtrationThe reaction product was suction-filtered off
  6. customdried
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9abee87c84db42d7b3ad4fc24405ea4c
Source dataset
uspto-grants-1976_08
Patent number
US03975524

Reaction notes

Loading…