Dimethylformamide → HCID 86755629, compound

HRID 1871439Notes

Reaction equation

HRID 1871439 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH:17]=[CH:18][CH2:19]3)[C:14](=[O:21])[N:13]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.C(=O)([O-])[O-].[K+].[K+].C[N:47](C=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH:17]=[CH:18][CH2:19]3)[C:14](=[O:21])[N:13]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:33][C:29](=[O:39])[C:30]3[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:32]([NH2:47])=[O:34])[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 86755626HCID 86755626, compound

Product 1

HCID 86755629HCID 86755629, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of compound 117, 10 g of phthalimide and 10 g of potassium carbonate was heated for 5 h at 100° C. in DMF. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by chromatography (dichloromethane) and crystallized from ethyl acetate/ether. M.p. 104°-105° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by chromatography (dichloromethane)
  5. customcrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-39b53e8bb4fa46288b23f23248314dfa
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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