Methanol → HCID 827024, compound

HRID 389024Notes

Reaction equation

HRID 389024 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH:5](Br)[CH:6](Br)[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9](=[O:12])[C:10]=2[CH:11]=1.C1CCN2C(=NCCC2)CC1.[CH3:30][OH:31]>>[Br:1][C:2]1[S:3][C:4]2[C:5]([O:31][CH3:30])=[CH:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9](=[O:12])[C:10]=2[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13913724HCID 13913724, compound

Product 1

HCID 827024HCID 827024, compound

Procedure

A methanol (1100 mL) solution of the compound obtained in Example 13 (90.2 g, 200 mmol) was refluxed while heating overnight. After allowing the mixture to cool in the air, DBU (63.4 g, 417 mmol) was further added thereto, and the mixture was refluxed while heating for another overnight. The reaction mixture was allowed to cool in the air, and the precipitated crystals were separated by filtration and dried, to give the captioned compound in an amount of 55.7 g, 173 mmol (2 steps, 87%).

Workup

  1. temperaturewhile heating overnight
  2. additionwas further added
  3. temperaturethe mixture was refluxed
  4. temperaturewhile heating for another overnight
  5. temperatureto cool in the air
  6. customthe precipitated crystals were separated by filtration
  7. customdried
  8. customto give the captioned compound in an amount of 55.7 g, 173 mmol (2 steps, 87%)

Sources & evidence

ORD record
ord-a0c05e51875948709153b08b7b3c6739
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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