Potassium Carbonate → HCID 14987128, compound

HRID 1493761Notes

Reaction equation

HRID 1493761 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:20]1([CH2:19][CH2:18][CH2:17][NH:16][C:13]([C:11]2[O:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)=[O:14])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61055N-(3-Aminopropyl)morpholineHCID 4769304HCID 4769304, compound

Product 1

HCID 14987128HCID 14987128, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.06 g of 5-(4-bromphenyl)-2-furancarboxylic acid chloride and 2.55 g of N-(3-aminopropyl)morpholine is refluxed 6 hr with 3.0 g of anhydrous potassium carbonate in 50 ml of acetonitrile. The mixture is allowed to stir at room temperature overnight. Solvents are then evaporated and the residue is triturated with ethyl ether followed by evaporation again. This process is repeated several times. A solution of the residue in ethyl ether is allowed to stand overnight whereupon crystals are formed. After three recrystallizations from ethyl acetate, the product, 2.47 g (37.5%), melts at 8°-100° C. The CI and EI mass spec. are consistent with the proposed structure. The latter showed M+ =393.

Workup

  1. customSolvents are then evaporated
  2. customthe residue is triturated with ethyl ether
  3. customfollowed by evaporation again
  4. waitto stand overnight whereupon crystals
  5. customare formed
  6. customAfter three recrystallizations from ethyl acetate

Sources & evidence

ORD record
ord-aa47776120134f0ca9f56bf4d77348c2
Source dataset
uspto-grants-1991_06
Patent number
US05023272

Reaction notes

Loading…