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Benzyl Bromide → 5-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 393595
Notes
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Reaction equation

HRID 393595 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH:5][CH:6]=[C:7]1[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])[O:9][C:8]1=[O:16].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:28]([O:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH:5][CH:6]=[C:7]1[C:12](=[O:13])[O:11][C:10]([CH3:14])([CH3:15])[O:9][C:8]1=[O:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 226465515-((3-Hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 226465295-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5-((3-hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (20 g, 69 mmol), potassium carbonate (12.4 g, 90 mmol) and benzyl bromide (15.4 g, 90 mmol) in DMF (100 ml) was heated at 65° C. for 2 hours. Two thirds of the DMF was removed from the mixture by evaporation, the mixture was diluted with water, adjusted to pH4 with 5M hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with water and then brine, dried (MgSO4) and the volatiles removed by evaporation. The solid residue was triturated with ether, and collected by filtration and dried under vacuum to give 5-((3-benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (22 g, 83%) as a cream solid.

Workup

  1. customTwo thirds of the DMF was removed from the mixture by evaporation
  2. additionthe mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customthe volatiles removed by evaporation
  7. customThe solid residue was triturated with ether
  8. filtrationcollected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-ca3bb5cda7084d30afd871c908917915
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06809097B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes