Cyanuric chloride → HCID 15379923, compound

HRID 1735126Notes

Reaction equation

HRID 1735126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][NH:8][CH2:7][CH2:6]2.[N:15]1[C:22](Cl)=[N:21][C:19](Cl)=[N:18][C:16]=1[Cl:17].[C:24](=[O:27])([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Cl:17][C:16]1[N:15]=[C:22]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)[N:21]=[C:19]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:27][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)[N:18]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 10340Sodium CarbonateHCID 156236,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline

Product 1

HCID 15379923HCID 15379923, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A vigorously stirred dispersion of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9.57 g, 40.4 mM) and cyanuric chloride (3.75 g, 20.2 mM) in dioxane (80 mL) was treated with sodium carbonate solution (0° C., 1M, 80 mL) at 0° C. for 0.5 hr then 4 hr at ambient temperature. Extraction with chloroform (4×70 mL), washing with saturated sodium chloride solution (80 mL), filtration through a cotton plug and concentration afforded an oil. Evaporation from benzene (2×40 mL) left a white foam which was triturated with hot methanol to provide a white crystalline solid, 9.35 g, (94%), mp=149°-151° C.

Workup

  1. custom4 hr
  2. customat ambient temperature
  3. extractionExtraction with chloroform (4×70 mL)
  4. washwashing with saturated sodium chloride solution (80 mL), filtration through a cotton plug and concentration
  5. customafforded an oil
  6. customEvaporation from benzene (2×40 mL)
  7. waitleft a white foam which
  8. customwas triturated with hot methanol
  9. customto provide a white crystalline solid, 9.35 g, (94%), mp=149°-151° C.

Sources & evidence

ORD record
ord-d0f8f5b1ef274133853ab56ee36066b5
Source dataset
uspto-grants-1996_07
Patent number
US05536722

Reaction notes

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