Water → HCID 15718665, compound

HRID 2165368Notes

Reaction equation

HRID 2165368 reaction equation
[CH:1]([N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:5]1[CH:20](Br)Br)([CH3:3])[CH3:2].C(=O)([O-])[O-:24].[Ca+2].O>C(O)C>[CH:1]([N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:5]1[CH:20]=[O:24])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10112Calcium CarbonateHCID 15718664HCID 15718664, compound

Product 1

HCID 15718665HCID 15718665, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g of the product of step 1, above, in 35 ml of 100% ethanol is mixed with 0.4g of calcium carbonate (powdered) and 15 ml of water. The mixture is refluxed for about 4 hours, then cooled, quenched with water and extracted with ethyl acetate. The extracts are dried and then evaporated to dryness to yield a dark amber gum, which is chromatographed on prep. plates, using petroleum ether/ether (85/15) and the largest (second of three) major band eluted with ethyl acetate to obtain the title product of this example as yellow solids, mp 95°-101°.

Workup

  1. temperatureThe mixture is refluxed for about 4 hours
  2. temperaturecooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. customThe extracts are dried
  6. customevaporated to dryness
  7. customto yield a dark amber gum, which
  8. customis chromatographed on prep
  9. washthe largest (second of three) major band eluted with ethyl acetate

Sources & evidence

ORD record
ord-964bd14043024711a384766a7a300f00
Source dataset
uspto-grants-1990_07
Patent number
US04939159

Reaction notes

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