Thiomorpholine → HCID 21518493, compound

HRID 1283581Notes

Reaction equation

HRID 1283581 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:13])[N:3]=1.[NH:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1>O1CCOCC1>[S:17]1[CH2:18][CH2:19][N:14]([C:2]2[C:11]3[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([Cl:13])[N:3]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 215184781,3-Dichloro-5-methylisoquinoline

Product 1

HCID 21518493HCID 21518493, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 23.3 gm (0.11 mol) of 1,3-dichloro-5-methyl-isoquinoline [prepared according to G. Simchen et al, Chem. Ber. 102, 3666 (1969); m.p. 120°C], 28.3 gm (0.275 mol) of thiomorpholine and 110 ml of dry dioxane was refluxed for 4 hours. The mixture was then evaporated, the residue was taken up with a mixture of tolune and water, and the toluene phase was isolated, dried and evaporated. The residue was recrystallized from 100 ml of ethyl acetate, yielding 22.7 gm (72% of theory) of the desired compound, m.p. 134°-136°C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe mixture was then evaporated
  3. additionthe residue was taken up with a mixture of tolune and water
  4. customthe toluene phase was isolated
  5. customdried
  6. customevaporated
  7. customThe residue was recrystallized from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-606c0b858b3646ebbc5074ae40e043e5
Source dataset
uspto-grants-1976_08
Patent number
US03975524

Reaction notes

Loading…