Chlorosuccinimide → HCID 178431913, compound

HRID 2250501Notes

Reaction equation

HRID 2250501 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[NH:11][C:12]([NH:14][C:15]2[C:19]([CH3:20])=[CH:18][S:17][CH:16]=2)=[NH:13])[O:4][CH2:3][CH2:2]1.[Cl:21]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:21][C:16]1[S:17][CH:18]=[C:19]([CH3:20])[C:15]=1[NH:14][C:12]([NH:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]21[O:1][CH2:2][CH2:3][O:4]2)=[NH:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178431887HCID 178431887, compound

Product 1

HCID 178431913HCID 178431913, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

N-(1,4-Dioxaspiro[4.5]dec-6-yl)-N′-(4-methylthiophen-3-yl)guanidine (49 mg) was dissolved in glacial acetic acid (3 ml), and a solution of N-chlorosuccinimide (20.3 mg) in glacial acetic acid (5 ml) was added slowly. The mixture was stirred for a number of hours and then allowed to stand at room temperature over the weekend, after which the glacial acetic acid was removed under reduced pressure, the residue was taken up in water and the mixture was adjusted to pH 10 using 2N sodium hydroxide solution. The basic phase was extracted three times with ethyl acetate and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative chromatography and the product-containing fractions were combined, freed from acetonitrile, made basic and extracted three times with ethyl acetate. The organic phases were combined, dried (MgSO4) and filtered. Removal of the solvent under reduced pressure gave 24 mg of the desired product which was used directly for the next step.

Workup

  1. customto stand at room temperature over the weekend
  2. customafter which the glacial acetic acid was removed under reduced pressure
  3. extractionThe basic phase was extracted three times with ethyl acetate
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative chromatography
  8. extractionextracted three times with ethyl acetate
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-88f0be389a9741e1a15f48032a1ad307
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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