Potassium Hydroxide → HCID 178456491, compound

HRID 703116Notes

Reaction equation

HRID 703116 reaction equation
BrC(Br)(C)C([O-])=O.[OH-].[K+].[O:10]=[C:11]1[N:19]([CH2:20][CH2:21][CH3:22])[C:18]2[NH:17][C:16]([C:23]3[CH:35]=[CH:34][C:26](/[CH:27]=[CH:28]/[C:29]([O:31]CC)=[O:30])=[CH:25][CH:24]=3)=[N:15][C:14]=2[C:13](=[O:36])[N:12]1[CH2:37][CH2:38][CH3:39]>O>[O:10]=[C:11]1[N:19]([CH2:20][CH2:21][CH3:22])[C:18]2[NH:17][C:16]([C:23]3[CH:35]=[CH:34][C:26]([C:27]#[C:28][C:29]([OH:31])=[O:30])=[CH:25][CH:24]=3)=[N:15][C:14]=2[C:13](=[O:36])[N:12]1[CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 17760438HCID 17760438, compoundHCID 178456492HCID 178456492, compound

Product 1

HCID 178456491HCID 178456491, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of the above dibromopropionate (3.00 g, 5.26 mmol) in an anhydrous ethanolic solution (150 ml) of potassium hydroxide (1.5 g, 26 mmol) was refluxed for 21 hours, then diluted over 3 hours with water (250 ml) as the ethanol was allowed to evaporate. The cooled solution was treated with 1N HCl until a precipitate formed (pH 10) which was extracted with methylene chloride (100 ml). The aqueous phase was made strongly acidic with 1N HCl. The thick precipitate was filtered and dried to yield a solid. A portion of this solid (0.65 g) was recrystallised from 50% ethanol (50 ml) to give the title compound as a yellow solid as the hemihydrate; mp slow dec. starting at 260° C. Analysis for (C20H20N4O4.5H2O): C,61.69; H,5.44; N,14.39. Found: C,61.85; H,5.38; N,14.45.

Workup

  1. temperaturewas refluxed for 21 hours
  2. customto evaporate
  3. additionThe cooled solution was treated with 1N HCl until a precipitate
  4. customformed (pH 10) which
  5. extractionwas extracted with methylene chloride (100 ml)
  6. filtrationThe thick precipitate was filtered
  7. customdried
  8. customto yield a solid
  9. customA portion of this solid (0.65 g) was recrystallised from 50% ethanol (50 ml)

Sources & evidence

ORD record
ord-35a8a27a35f749b5abd1919a4cc7938d
Source dataset
uspto-grants-1991_01
Patent number
US04981857

Reaction notes

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